Name: 18728-61-5|1-(Pyridin-2-yl)ethanol|98%
Brand: Ambeed
SKU: A109607
Price: 10.0 USD
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1
[ 1122-62-9 ]
1-(pyridine-2-yl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With anhydrous magnesium perchlorate; polymer-bound NADH (2a) In acetonitrile; benzene at 80℃; for 120h; Further byproducts given;
100%	With polimer supported sodium borohydride In methanol at 20℃; for 72h;	24 The 1-pyridin-2-ylethanol used as starting material was prepared as follows : - To l-pyridin-2-ylethanone (600 mg, 3. 18 mmol) in methanol (10 mL) was added polymer supported sodium borohydride (3.0 g, 9.92 mmol) and the reaction was stirred at room temperature for 72 h. The reaction was filtered and the filtrates were evaporated to give the 1- pyridin-2-ylethanol as colourless oil (630 mg, quantitative); NMR Spectrum : (DMSOd6) 1.38 (d, 3H), 4.71 (q, 1H), 5.30 (br, 1H), 7.21 (m, 1H), 7.50 (d, 1H), 7.75 (m, 1H), 8.47 (1H, d); Mass Spectrum: M+H+ 192.
100%	With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amide](carbonyl)(hydride)iron(II); hydrogen In tetrahydrofuran at 50℃; for 4h; Glovebox; chemoselective reaction;

100%	With [(CH₂(NC(C₆H₅)N(C₄H₉)CHC)2)RhI₂((C₆H₅)2PC₂H₄P(C₆H₅)2)]⁽¹⁺⁾*I^(1-)=[(CH₂(NC(C₆H₅)N(C₄H₉)CHC)2)RhI₂((CH₂P(C₆H₅)2)2)]I; isopropanol; potassium hydroxide In water monomer for 24h; Reflux;
99%	With stannous trifluoromethanesulfonate; PMHS; 2,6-bis(4,5-dihydrooxazol-2-yl)pyridine In methanol at 20℃; for 14h;
99%	With formic acid; triethylamine In ethyl acetate at 24℃; for 18h;
99%	With lithium isopropoxide In isopropanol at 180℃; for 0.333333h; microwave irradiation;
99%	With formic acid; triethylamine In ethyl acetate at 25℃; for 15h; Inert atmosphere;
99%	With [(iPr-PNP)Fe(H)(CO)(η1-BH4)]; hydrogen In ethanol at 40℃; for 6h; Inert atmosphere;
99%	With hydrogen In ethanol at 120℃; for 16h; Autoclave;
99%	With C₂₅H₃₀ClIrN₂O₃; water monomer; potassium hydroxide In isopropanol for 1h; Reflux;
98%	With potassium hydroxide; isopropanol for 10h; Heating;
98%	With formic acid; C₁₈H₂₄ClIrN₃ In water monomer at 80℃; for 12h; Schlenk technique; Inert atmosphere; chemoselective reaction;
97%	With isopropanol; lithium tert-butylate at 180℃; for 0.5h;
97%	With trimethylamine-N-oxide; (N,N,N-trimethyl-2-(5-oxo-4,6-bis(trimethylsilyl)cyclopenta[c]pyrrol-2-(1H,3H,5H)-yl)ethanaminium) iron tricarbonyl; hydrogen In water monomer at 85℃; for 14h; Autoclave; Inert atmosphere;
97%	With [Re(NH{CH₂CH₂P(iPr₂)}₂)(CO)₃]Br; potassium-t-butoxide; hydrogen In toluene at 110℃; for 17h; Inert atmosphere; Glovebox; Autoclave;
96%	With isopropanol at 85℃; for 24h; Inert atmosphere;
96%	With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H₂O); hydrogen In tert-Amyl alcohol at 30℃; for 12h; Green chemistry;	4.2. General procedure for catalytic hydrogenation of 2 General procedure: To an oven-dried 5 mL round-bottom flask were added ketone (1 mmol), cat. 7 (2.7 mg, 0.5 mol %) and tert-amyl alcohol (1 mL). Next, vacuum was applied to the flask followed by filling with H2 gas and keeping the flask attached to a balloon filled with H2 gas. The mixture was heated at 30 °C for 12 h. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. The alcohols were isolated and purified by filtering a hexanes/ethyl acetate (5:1) solution of the crude product through a pad of silica gel, and then removing the solvent under reduced pressure. The conversion and purity of the alcohol products was assessed using NMR spectroscopy.
96%	With methanol; [Cp*Ir(2,2'-bpyO)(OH)][Na] at 66℃; for 12h; Inert atmosphere; Schlenk technique;
95%	With sodium tetrahydridoborate; poly[N-(2-aminoethyl)acrylamido]trimethyl ammonium chloride In tetrahydrofuran; water monomer at 20℃; for 0.75h;
93%	With benzyltriphenylphosphonium tetraborate In methanol at 20℃; for 0.0833333h;
93%	With [(N,N′-bis(diisopropylphosphino)-2,6-diaminopyridine)Mn(CO)₃][Br]; potassium-t-butoxide; hydrogen In toluene at 130℃; for 38h; Glovebox; Autoclave;	2.2. Typical catalytic hydrogenation General procedure: In a glove box, an autoclave was charged with the desired ketone (0.5 mmol), toluene (2 mL), Mn complex 1 (14 mg, 5 mol%) followed by t-BuOK (5.6 mg, 10 mol%), in this order. The autoclave is then closed and charged with H2 (50 bar).
93%	With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H₂O); isopropanol at 82℃; for 6h; Inert atmosphere; Green chemistry;	15 1-(Pyridin-2-yl)ethanol The 2 - acetyl pyridine (121 mg, 1.0 mmol), cat. [Ir] (1.1 mg, 0 . 002 mmol, 0.2 μM %) and isopropyl alcohol (5 ml) are added to the 25 ml Kjeldahl tube, N2Protection Cooling to room temperature, rotary evaporation to remove the solvent, then through the column chromatography (developing solvent: petroleum ether/ethyl acetate) to obtain the pure target compound, yield: 93%
93%	With [Cp*Ir(2,2'-bpyO)(OH)][Na]; hydrogen In water monomer at 30℃; for 12h; Green chemistry;	4.1. General procedure for catalytic hydrogenation of ketones,aldehydes or unsaturated aldehydes General procedure: To an oven-dried 5 mL round-bottom flask were added ketonesor aldehydes or unsaturated aldehydes (1 mmol), cat. 6 (5.5 mg,1 mol %) and H2O (1 mL). Next, vacuum was applied to the flask followedby filling with H2 gas and keeping the flask attached to a balloonfilled with H2 gas. The mixture was heated at 30 °C for 12 h.After completion of the reaction, the mixture was extracted withethyl acetate (5 mL x 3). Then, the ethyl acetate layers were combined, dried with anhydrous sodium sulfate, filtered, and concentratedby evaporation under reduced pressure. The alcohols wereisolated and purified by filtering a hexanes/ethyl acetate (8:1)solution of the crude product through a pad of silica gel. Thenthe solvent was removed under reduced pressure to afford the correspondingproducts. The purity of alcohol products was assessedusing 1H NMR spectroscopy.
93%	With [Cp*Ir(2,2'-bpyO)(OH)][Na]; hydrogen In water monomer at 30℃; for 12h;	17 The method is: 2-Acetylpyridine (121 mg, 1.0 mmol), metal ruthenium complex [Cp*Ir(2,2'-bpyO)(OH)][Na] (4.6 mg, 0.01 mmol, 1 mol %) and water (1 mL) sequentially added to 25 ml round bottom flasks, and replace the air in the round bottom flask with hydrogen. The pressure of hydrogen gas in the system during the entire process of the reaction was 1 standard atmospheric pressure, and the reaction mixture was reacted at 30 °C, the hydrogen atmosphere was 12 h. After the reaction is completed, the solvent is removed by rotating, then the pure target compound is obtained by column chromatography (eluent: petroleum ether / ethyl acetate = 6:1), yield: 93%.
92%	With sodium tetrahydridoborate In methanol at 25℃; for 16h; Cooling with ice;	1.1 Step 1: Synthesis of 1-(pyridin-2-yl)ethanol. To an ice-cooled solution of 1-(pyridin-2-yl)ethanone (11 g, 91 mmol) in methanol(120 mL) was slowly added sodium borohydride (8.58 g, 227 mmol). Upon completeaddition, the mixture was warmed to 25 °C. After 16 h, the reaction was diluted with water(100 mL), and the mixture was concentrated in vacuo. The resulting aqueous solution wasextracted with ethyl acetate (3 x 100 mL). The combined organic extracted were washed withsaturated aqueous sodium chloride (2 x 50 mL), dried over anhydrous sodium sulfate,filtered, and concentrated. Purification by flash column chromatography (1 0-30% ethyl acetate in petroleum ether) afforded 1-(pyridin-2-yl)ethanol (10.3 g, 92% yield). 1H NMR (400 MHz, Chloroform-d) ö: 8.54 (d, I = 4.8 Hz, 1 H), 7.72 - 7.68 (m, 1 H), 7.30 (d, I = 8.0 Hz, 1 H), 7.22-7.20 (m, 1 H), 4.93 -4.88 (m, 1 H), 4.39 (br s, 1 H), 1.52 (d, I = 6.4 Hz, 3 H).
92%	With (4-NHCpr)Triaz(NHP<SUP>i</SUP>Pr<SUB>2</SUB>)<SUB>2</SUB>Mn(CO)<SUB>2</SUB>Br; potassium-t-butoxide; hydrogen In toluene at 80℃; for 4h; Inert atmosphere; Autoclave;
92.9%	With C₄₀H₃₇ClN₂PRuS⁽¹⁺⁾*C₂₄H₂₀B^(1-); isopropanol; potassium hydroxide at 82℃; for 2h;	2.6. Typical procedure for transfer hydrogenation of ketones General procedure: The mixture of a ketone (0.2 mmol) and base (0.08 mmol)containingthe catalyst (0.1 mol%) in 2-propanol (6 ml) was stirred at82 °C. After the reactionwas complete, diethyl ether could be addedto the mixture and extract the ruthenium complexes followed byfiltration and neutralized with 1N HCl, washed with water anddried over anhydrous Na2SO4. Conversion obtained is related to theresidual unreacted ketone. Percentage of conversionwas calculatedby using GC method of the crude mixture and compared with theauthentic samples. Acetone was identified as only by-product in allthe cases. As the catalyst is stable in all organic solvents and it canbe recovered and the work up process is also very simple for thiscatalytic system.
92%	Stage #1: 2-acetylpyridine With pyridine N-oxide; Triethoxysilane; C₂₇H₄₇FeP₃Si In tetrahydrofuran at 50℃; for 6h; Schlenk technique; Stage #2: With sodium hydroxide In tetrahydrofuran; methanol at 60℃; for 24h; Schlenk technique;
91%	Stage #1: 2-acetylpyridine With n-butyllithium; 1-(2-hydroxyethyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate; ferrous acetate In tetrahydrofuran at 65℃; for 1h; Inert atmosphere; Stage #2: With water monomer; sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h; Inert atmosphere;
91%	With sodium tetrahydridoborate In methanol at 20℃; for 12h;
91%	With sodium tetrahydridoborate In methanol at 0 - 20℃; for 12h;
90%	With sodium tetrahydridoborate In ethanol for 2h; Heating;
90%	Stage #1: 2-acetylpyridine With C₃₉H₄₆ClCuN₂; phenylsilane; potassium-t-butoxide In tetrahydrofuran at 20℃; for 0.416667h; Schlenk technique; Inert atmosphere; Glovebox; Stage #2: With water monomer; sodium hydroxide In tetrahydrofuran; methanol for 1h; Schlenk technique; Glovebox; chemoselective reaction;
90%	With BH₃; (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole In tetrahydrofuran; 2-methyltetrahydrofuran at 0℃; Flow reactor; Green chemistry;
89%	With potassium hydroxide In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; Schlenk technique; Glovebox; chemoselective reaction;
89%	Stage #1: 2-acetylpyridine With bis-[N,N′-bis(2,6-(di-isopropyl)phenyl)imidazol-2-ylidene]-(1H-1,2,4-triazol-1-yl)}copper(I) In tetrahydrofuran at 55℃; for 16h; Stage #2: With sodium hydroxide In methanol; water monomer at 25℃; for 1.5h;
89%	With Mn(CO)<SUB>3</SUB>Br(k<SUP>2</SUP>P,N-Ph<SUB>2</SUB>PN(H)Py); hydrogen; 1,1,1,3,3,3-hexamethyldisilazane potassium In toluene at 80℃; for 20h; Glovebox; Autoclave; Inert atmosphere;
89%	Stage #1: 2-acetylpyridine With C₃₆H₃₆FeN₆ at 20℃; for 22h; Inert atmosphere; Glovebox; Stage #2: With water monomer; sodium hydroxide for 1.5h;
87%	With hydrogen In toluene at 25℃; for 8h;
86%	With methanol; sodium tetrahydridoborate at 20℃; for 4h;
85%	With dodecane; Triethoxysilane; hydridoiron(II) (trimethylphosphane)3(benzophenone imine) In tetrahydrofuran at 55℃; for 2h; Schlenk technique; Inert atmosphere;
85%	Stage #1: 2-acetylpyridine With bis(η5-cyclopentadienyl) titanium dichloride; sodium tetrahydridoborate In 1,2-dimethoxyethane at 20℃; Stage #2: With sodium hydroxide In 1,2-dimethoxyethane
85%	With methanol; sodium tetrahydridoborate In tetrahydrofuran at 0℃; Inert atmosphere;
83%	Stage #1: 2-acetylpyridine With diphenylsilane; Cs₂CO₃ at 80℃; for 5h; Schlenk technique; Stage #2: With sodium hydroxide In methanol; water monomer at 70℃; Schlenk technique; chemoselective reaction;
82%	With sodium tetrahydridoborate In ethanol at 0 - 20℃;
80%	With Triethoxysilane; C₄₃H₄₈FeP₄ In tetrahydrofuran at 50℃; for 16h;
80%	With ammonia hydrochloride; zinc powder In tetrahydrofuran; water monomer at 60℃; for 4h;
80%	With C₁₂H₁₂MnO₄⁽¹⁺⁾*BF₄^(1-); potassium-t-butoxide In isopropanol at 90℃; for 24h; Schlenk technique; Inert atmosphere;
80%	With methanol; bis[dichlorido(η⁵-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; 6,6′-dihydroxy-2,2′-bipyridine; potassium hydroxide at 60℃; for 24h; Inert atmosphere;
79%	With C₅₆H₅₅ClN₃P₂Ru⁽¹⁺⁾*F₆P^(1-); potassium 2-methyl-2-butoxide In isopropanol at 20 - 80℃; for 1.5h; Schlenk technique; Inert atmosphere;
79%	With hydrogen; anhydrous silver perchlorate; 1,1,1,3,3,3-hexamethyldisilazane potassium In toluene at 25℃; for 17h; Glovebox;
78%	With potassium hydroxide; 18-crown-6 ether; hydrogen; isopropanol at 75℃; for 6h;
78%	Stage #1: 2-acetylpyridine With ferrous acetate; tricyclohexylphosphine In tetrahydrofuran at 65℃; Inert atmosphere; Stage #2: In tetrahydrofuran at 65℃; Inert atmosphere; Stage #3: With water monomer; sodium hydroxide In tetrahydrofuran; methanol at 0 - 20℃; Inert atmosphere;
73%	With cis-[(H)(SePh)Fe(PMe₃)₄]; sodium tertiary butoxide In isopropanol at 80℃; for 24h;
72%	Stage #1: 2-acetylpyridine With C₄₀H₃₂Cl₂N₃PRu; isopropanol at 82℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: With sodium hydroxide for 4h; Schlenk technique; Inert atmosphere;
70%	With sodium tetrahydridoborate In methanol at 20℃; for 5h;
70%	With sodium tetrahydridoborate In water monomer at 90℃; for 1.25h;	Synthesis of α-methyl-2-pyridinemethanol. General procedure: 20 g (0.17 mol) of 2-acetyl-pyridine were dissolved in 250 mL of EtOH. 12.5 g (0.3 mol) of NaBH4 were added slowly. After 1h at room temperature, the conversion of the substrate was complete. 250 mL of water were added and the solution was heated at 90°C for 15 min. After cooling, the product was extracted with AcOEt. The combined organic solutions were dried over MgSO4,the solvent was evaporated to give 13g (70%) of α-methyl-2-pyridine methanol as a pale green oil. 1H NMR (250 MHz, CDCl3): (ppm) = 1.49 (3H, d, J = 6 Hz); 4.94 (1H, q, J = 6 Hz); 7.21 (1H, m);7.28 (1H, m); 7.73 (1H, m); 8.48 (1H, m). Purity = 99% (NMR).
70%	Stage #1: 2-acetylpyridine With Triethoxysilane; [cis-Fe(H)(SPh)(PMe₃)₄] In tetrahydrofuran at 60℃; for 24h; Stage #2: With methanol; sodium hydroxide In tetrahydrofuran; water monomer at 60℃; for 24h;	2.2. General procedure for catalytic hydrosilylation of aldehydes General procedure: To a 25 mL Schlenk tube containing a solution of 1 in 2 mL of THF was added an aldehyde (1.0 mmol) and (EtO)3 SiH (0.20 g, 1.2 mmol). The reaction mixture was stirred at 50-55 °C until there was no aldehyde left (monitored by TLC and GC-MS). The reaction was then quenched byMeOH (2mL) and a 10% aqueous solution of NaOH (5 mL) with vigorous stirring at 60 °C for about 24 h.The organic product was extracted with diethyl ether (10 mL × 3), dried over anhydrous MgSO4, and concentrated under vacuum. The alcohol product was further purified using flash column chromatography (elute with 5-10% ethyl acetate in petroleum ether). The 1H NMR and 13C NMR spectra of the alcohol products are providedin Supporting information.
69%	With sodium tetrahydridoborate In methanol; dichloromethane at 20℃; for 6h;
66%	With Triethoxysilane; C₂₇H₄₂FeP₄S In tetrahydrofuran at 50℃; for 24h; Schlenk technique; Green chemistry;
63%	With dicarbonyl-(2,4-bis(trimethylsilyl)bicyclo[3.3.0]nona-1,4-dien-3-one)[acetonitrile]iron; isopropanol at 80℃; for 18h; Inert atmosphere;
56.1%	With methanol; sodium tetrahydridoborate at 20℃; for 18h;	35 1-Pyridin-2-yl-ethanol 1-Pyridin-2-yl-ethanol 2-Acetylpyridine (1.0 g, 8.26 mmol) was dissolved in anhydrous methanol (20 mL) and treated with sodium borohydride (0.62 g, 16.51 mmol) and stirred at ambient temperature 18 hours. A saturated solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The combined organics were washed with water and brine, dried over anhydrous sodium sulfate, evaporated and chromatographed using a gradient of 50 to 100% ethyl acetate in hexanes to provide 0.57 g (56.1%) of the title compound. MS m/z 124 (M+H)+.
50%	With anhydrous magnesium perchlorate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In acetonitrile at 70℃; for 168h;
37%	With C₅₁H₄₆N₃OP₂Ru; potassium hydroxide In isopropanol at 80℃; for 2h;	2.5. Catalysis: general procedure for the transfer hydrogenationreactions General procedure: A mixture of ketone (1 mmol), a known mole percent of the catalystand KOH (0.06 mmol) was dissolved in 2-propanol (5 mL), and the mixture was heated under reflux for the desired period oftime. The catalyst was removed as precipitate from the reactionmixture by the addition of diethyl ether followed by filtrationand subsequent neutralization with 5 mL of 1 M HCl. Then theether layer was passed through a short path of silica gel and the filtratewas subjected to GC analysis for identification andquantification.
35%	Stage #1: 2-acetylpyridine With (dppe)2Fe(H)2*(C₇H₈)2; Na-tetrakis(ethoxy)borate In toluene at 100℃; for 2h; visible light irradiation; Inert atmosphere; Stage #2: With water monomer; sodium hydroxide In methanol; toluene at 20℃; for 16h;
20%	With sodium tetrahydridoborate In methanol at 20℃;
	With hydrogenchloride; zinc,^6a mercury,^6b
	With sodium tetrahydridoborate Yield given;
	With sodium tetrahydridoborate In methanol Ambient temperature;
	With sodium tetrahydridoborate
	With sodium tetrahydridoborate In methanol for 0.5h;
	With sodium tetrahydridoborate
	Stage #1: 2-acetylpyridine With sodium tetrahydridoborate In methanol at 0℃; for 4h; Stage #2: With methanol; water monomer	11.1 Production Example 11-1: 1-(Pyridin-2-yl)ethanol: A methanol solution (100 mL) of 1-pyridin-2-ylethanone (10.0 g) was cooled to 0°C, sodium borohydride (6.2 g) was added thereto and stirred at that temperature for 4 hours. Then water was added to the reaction solution, and the organic solvent was evaporated off under reduced pressure. The resulting residue was extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated off under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate = 4/1 to 3/2) to obtain the entitled compound (9.0 g).
	With potassium hydroxide; Au/TiO₂; isopropanol at 82℃; for 8h; Inert atmosphere; chemoselective reaction;
	With ethanol; CF₃O₃S^(1-)*C₄₈H₃₈NO₃PRh⁽¹⁺⁾; potassium carbonate at 40℃;
	With sodium tetrahydridoborate In ethanol Inert atmosphere;
99 %Spectr.	With hydrogen In 1-butyl-3-methylimidazolium hexafluorophosphate at 20℃; for 24h;	General procedure: The palladium nanoparticles on SWNTs were prepared in [BMIM][PF6]. The SWNTs (5 mg) was grounded in IL (1 ml) for 30 min, and then Pd(II) acetate (0.018 mmol) was dissolved in the solution. The Pd(II) acetate was in situ reduced in IL with 1 atm of hydrogen for 5 min at room temperature. The aryl ketone (0.3 mmol) was added to this solution under 1 atm of hydrogen at room temperature. After the >99% completion of the reaction was checked by TLC, the products were extracted with ethyl ether. The ethereal phase was concentrated and analyzed by 1H NMR.
98 %Spectr.	With potassium fluoride; palladium diacetate; chlorobenzene In tetrahydrofuran; water monomer at 20℃; for 1h; Inert atmosphere; chemoselective reaction;
87 %Chromat.	With [(iPrPNP)FeH(CO)Br]; potassium-t-butoxide; hydrogen In ethanol at 26 - 28℃; for 15h;
	With Ru(P,O,P-xantphos)(S-dmso)Cl₂; isopropanol; potassium hydroxide for 12h; Reflux;
18 %Chromat.	With anhydrous sodium carbonate; isopropanol at 82℃; for 8h; Inert atmosphere;
99 %Chromat.	With C₇₁H₅₆N₅P₂Ru⁽¹⁺⁾*Cl^(1-); potassium isopropoxide; isopropanol at 82℃; for 6h; Inert atmosphere;
99 %Chromat.	Stage #1: 2-acetylpyridine With [RuCl2(η6-benzene)tris(4-methoxyphenyl)phosphane] In isopropanol at 82℃; for 0.166667h; Inert atmosphere; Stage #2: With potassium isopropoxide In isopropanol at 82℃; for 9h; Inert atmosphere;
	Multi-step reaction with 2 steps 1: C₂₄H₅₀FeO₂P₄ / tetrahydrofuran / 36 h / 50 °C / Inert atmosphere 2: water monomer; sodium hydroxide / tetrahydrofuran; methanol / 48 h / 50 °C
> 99 %Chromat.	With acetonitrile(η5-pentamethylcyclopentadienyl)(κ2-C,N-3-methyl-1-(2-picolyl)imidazol-2-ylidene)ruthenium(II) hexafluorophosphate; isopropanol; potassium hydroxide at 82℃; for 3h; Inert atmosphere;
	With sodium tetrahydridoborate In methanol at 60℃; for 6h;
	With C₅₅H₄₁ClN₂O₃P₂Ru; isopropanol; potassium hydroxide In 1,3-dimethylbenzene at 20 - 82℃; for 4h; Inert atmosphere;	Typical procedure for transfer hydrogenation of ketones General procedure: In an oven-dried round bottom flask, were placed ketone (2.4 mmol), catalyst (3 mol), base (12 mol), internal standard (m-xylene, 30 L, 0.24 mmol) and i-PrOH (5 mL) at room temperature. The reaction mixture was heated at 82 °C for the required reaction time under an atmosphere of nitrogen. Aliquots (0.2 mL) were taken at fixed time and the catalyst removed as precipitate from the reaction mixture by the addition of diethyl ether. The organic layer was neutralized with 1 N HCl, washed with water and dried over anhydrous Na2SO4. The combined organic layer passed through a short path of silica gel and then subjected to GCMS analysis. The conversions obtained are related to the residual unreacted ketone and are averages of two runs in the case of all catalytic reactions.
	With sodium tetrahydridoborate
79 %Spectr.	With trans-RuCl(6,6'-dihydroxyterpyridine)(PPh<SUB>3</SUB>)<SUB>2</SUB>PF<SUB>6</SUB>; potassium-t-butoxide; isopropanol at 80℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;
99 %Spectr.	With C₂₄H₂₀B^(1-)*C₄₀H₄₃NO₂PRuS⁽¹⁺⁾; isopropanol; potassium hydroxide at 80℃; for 12h; Inert atmosphere;	4.5 Typical procedure for the catalytic transfer hydrogenation of ketones General procedure: In a dry two-necked round bottom flask under an atmosphere of nitrogen were placed an appropriate amount of catalyst 1-5 (0.01 mmol), (0.025 mmol) of KOH and (10 mmol) of aryl ketone in 2-propanol (10 ml) was added and the resulting mixture was refluxed under an atmosphere of nitrogen and the course of the reaction was monitored by 1H NMR analysis. After completion of the reaction, the solvent was removed under reduced pressure. The catalyst was removed by the addition of 15 ml of ether (b.p., 40-60 °C) followed by filtration and subsequent neutralization with dilute HCl. The combined organic fractions were dried over anhydrous Na2SO4. The solvent was distilled off to obtain a crude mixture containing ketone and its hydrogenated product. Percentage conversion was calculated by 1H NMR spectra of the crude mixture. The only side product formed is acetone, which is easily removed by distillation during workup.
	With [(bis(5-methyl-3-phenyl-1,2,4-triazolyl)(3-methyl-5-phenyl-1,2,4-triazolyl)borate)Ru(p-cymene)Cl]; potassium hydroxide In isopropanol for 24h; Inert atmosphere; Reflux;
	Multi-step reaction with 2 steps 1: mer-hydrido(2-mercaptobenzoyl)tris(trimethylphosphine)cobalt(III) / tetrahydrofuran / 8 h / 55 °C / Inert atmosphere 2: sodium hydroxide / tetrahydrofuran; water monomer / 56 h / 50 °C / Inert atmosphere
	With methanol In toluene at 20℃; for 4.5h; Inert atmosphere; Sealed tube; Irradiation;
	With RuCl(CH₃(C₆H₄)CH₃CHCH₃)((C₅H₄N)C₂N₃(CH₃)2)⁽¹⁺⁾*CF₃SO₃^(1-) = [RuCl(CH₃(C₆H₄)C₃H₇)((C₅H₄N)C₂N₃(CH₃)2)](CF₃SO₃); potassium hydroxide In isopropanol for 24h; Reflux;
	With potassium-t-butoxide In isopropanol at 90℃; for 0.533333h; Flow reactor; Inert atmosphere;
99 %Spectr.	With [Fe(N,N′-bis(diisopropylphosphino)-2,6-diaminopyridine)(H)(CO)Br]; potassium-t-butoxide; hydrogen In ethanol at 25℃; for 1h;
	With C₅₄H₄₁Cl₂N₂O₂P₂Ru; isopropanol; potassium hydroxide at 82℃; for 5h;	Typical procedure for transfer hydrogenation of ketones General procedure: The mixture of a ketone (0.2 mmol) and base (0.08 mmol) containing the catalyst (0.002 mmol) in i-PrOH (6 ml) was stirred at 82 °C. After the reaction was complete, diethyl ether could be added to the mixture and extract the ruthenium complexes followed by filtration and neutralized with 1 N HCl, washed with water and dried over anhydrous Na2SO4. Conversion obtained is related to the residual unreacted ketone. The alcohol products were identified by comparison with the authentic samples. Acetone was identified as only by-product in all the cases. As the catalyst is stable in all organic solvents and it can be recovered and the work up process is also very simple for this catalytic system.
	With 1-butyl-2,3-dimethylimidazolium hydroxide; hydrogen at 30℃; for 15h; Autoclave; chemoselective reaction;
	With C₁₀H₁₄Cl₃Ru^(1-)C₁₉H₁₅Cl₃N₃⁽¹⁺⁾H₂O; potassium hydroxide In isopropanol at 82℃; for 4h;

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2
1-(pyridine-2-yl)ethanol [ No CAS ]
[ 108-05-4 ]
[ 59042-90-9 ]
(R)-1-(2-pyridinyl)ethyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 46% 2: 47%	With 4 A molecular sieve In di-isopropyl ether for 4h; Ambient temperature; Candida antarctica lipase presence;
1: 33% 2: 41%	In various solvent(s) for 40h; Ambient temperature; lipase from Pseudomonas sp. (SAM II);
	With novozyme-435; 4 A molecular sieve In diethyl ether at 20℃; for 5h;

> 99 % ee

With Candida antarctica lipase B In toluene Resolution of racemate;

Reference： [1]Uenishi, Jun'ichi; Hiraoka, Takao; Hata, Shinichiro; Nishiwaki, Kenji; Yonemitsu, Osamu; Nakamura, Kaoru; Tsukube, Hiroshi [Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2481 - 2487]
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[4]Mazuela, Javier; Pàmies, Oscar; Diéguez, Montserrat [Chemistry - A European Journal, 2013, vol. 19, # 7, p. 2416 - 2432]

3
[ 18728-61-5 ]
[ 1122-62-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 9-azabicyclo[3.3.1]nonan-3-one N-oxyl; oxygen; HNO₃; NaNO₂ In acetonitrile at 20℃; for 3h;
93%	With sodium trifluoro-methanesulfinate In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;
91%	With (NH₄)₄[CuMo₆O₁₈(OH)₆]·5H₂O; oxygen; sodium chloride In lithium hydroxide monohydrate; acetonitrile at 60℃; for 24h;

90%	With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.5h; Heating;
90%	With 5H₃N5H⁽¹⁺⁾IMo₆O₂₄^(5-); oxygen; sodium chloride In lithium hydroxide monohydrate; acetonitrile at 70℃; for 24h; Green chemistry;
87%	With di-isopropyl azodicarboxylate; 9-azanoradamantane N-oxyl; glacial acetic acid In dichloromethane at 20℃; for 8h;
87.4%	With 9-azanoradamantane N-oxyl; di-isopropyl azodicarboxylate; glacial acetic acid In dichloromethane for 8h; Reflux;	8.o Example 8: Oxidation of alcohols using diisopropyl dicarboxylate (DIAD) as bulk oxidant; (o) Oxidation of 2-(1-hydroxyethyl)pyridine 2:4,5.di-O-isopropylidene-β-fructopyranose 2-(1-Hydroxyethyl)pyridine (76.8 mg, 0.624 mmol) was oxidized in the same manner as that described in Example 8, (a) (except that Nor-AZADO was used at 3 mol %, and the reaction was performed at room temperature) to obtain the objective compound (66.0 mg; yield, 87.4%). The spectrum data were found to be the same as those obtained in Example 6, (h). A solution of 4-phenylbutan-2-ol (97.7 mg, 0.651 mmol), Nor-AZADO (0.90 mg, 6.51 µmol, 1 mol%) and acetic acid (37 µl, 0.651 mmol) in dichloromethane (0.65 ml) was added with DIAD (128 µl, 0.651 mmol, 1 equivalent), and the mixture was stirred for 8 hours under reflux by heating. The reaction mixture was added with saturated aqueous sodium carbonate (2 ml), and the mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the objective compound (95.1 mg; yield, 99%). The spectrum data were found to be the same as those obtained in Example 5, (b).
86%	With oxygen In toluene at 79.84℃; for 4h;
86%	With 9H-fluoren-9-one; oxygen In dimethyl sulfoxide at 20℃; Irradiation;
83%	With Peroxyacetic acid
83%	With C₃₂H₂₅Cl₂N₆O₂Rh₂⁽¹⁺⁾*Cl^(1-); sodium hydroxide In lithium hydroxide monohydrate at 100℃; for 16h; Sealed tube; Green chemistry;
82%	With copper(II) selenite dihydrate; potassium hydroxide In toluene for 29h; Reflux;
81%	With 9-azanoradamantane-N-oxyl; glacial acetic acid; NaNO₂ In acetonitrile at 20℃; for 3h; air;
80%	With potassium peroxomonosulfate; sodium 2-iodobenzenesulfonate In acetonitrile at 70℃; for 12h;
78%	With Bi(NO₃)₃·5H₂O; 9-azabicyclo[3.3.1]nonan-3-one N-oxyl In acetonitrile at 65℃; for 2h; Schlenk technique;	3.2. General Procedure General procedure: Alcohols (1 mmol), Keto-ABNO (5 mol%, 0.05 mmol), Bi(NO3)35H2O (10 mol%,0.1 mmol), and 2 mL CH3CN were added to a 10 mL Schlenk tube equipped with amagnetic stirrer. Next, the mixture was stirred at 65 C for 2 h under air-balloon conditions.The progress of the reaction was monitored by TLC. After completion of the reaction, thesolution was diluted with ethyl acetate and washed with water, before the organic layerwas separated and dried over anhydrous MgSO4. The solvent was concentrated underreduced pressure and the crude product was purified by column chromatography on silicagel using PE/EtOAc as eluent to afford the pure products. All products were characterizedby 1H-NMR and 13C-NMR (Supplementary Materials).
76%	With oxygen; sodium hydride In tetrahydrofuran at 0 - 20℃; for 6h;	4.2. Aerobic oxidation of secondary aryl alcohols General procedure: A round-bottom flask that was flame-dried and cooled under dry air or oxygen atmosphere was charged with alcohol 6 or 33 (0.5 mmol) and THF (2.5 mL). After stirring at 0 °C for 5 min, NaH powder (1 mmol, 2 equiv) was added in one portion, and the mixture was allowed to warm to room temperature. The reaction was quenched by addition of saturated NH4Cl (2 mL) after the indicated time, extracted with EtOAc (10 mL×2), and washed by brine (15 mL). The combined organic phase was dried over MgSO4, the solvent was removed under vacuum, and the residue was purified by flash chromatography on silica gel to give the desired ketone product 7 and 34. For isolations of acids 8 and 35/36: the combined aqueous phase was acidified with 2 M HCl, and then extracted with EtOAc (10 mL×2) and washed by brine (15 mL). The combined organic phase was dried over Na2SO4, the solvent was removed under vacuum to give acid product that can be further purified by flash chromatography on silica gel.
75%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium-t-butoxide; copper trifluoromethanesulfonate; (S)-(-)-5-(2-pyrrolidinyl)-1H-tetrazole In N,N-dimethyl-formamide at 25℃; for 12h;	4 4.1.1. The oxidation of secondary alcohols General procedure: A round-bottom flask was charged with alcohol (2 mmol), CuOTf (0.1 mmol, 0.05 equiv) (S)-5-(pyrrolidin-2-yl)-1H-tetrazole (0.1 mmol, 0.05 equiv), TEMPO (0.1 mmol, 0.05 equiv), t-BuOK (2 mmol, 1 equiv) and DMF (5 ml). The reaction mixture was stirred at 25 °C open to air until the completion of the reaction, as monitored by TLC. The mixture was then diluted with CH2Cl2 (20 ml), washed with water, dried over Na2SO4, and evaporated under vacuum to give the crude product, which was purified by column chromatography to give the pure product.
75%	With sodium chlorine monoxide; N-chloro-succinimide; dimethyl sulfoxide; triethylamine In dichloromethane; lithium hydroxide monohydrate at -10 - 30℃; for 0.0569444h;	63 Example 61 Integrated Reaction Process of Corey-Kim Oxidation Reaction and Deodorization Step Using Microreactor 10267] The reaction step and the deodorization step wereperformed using the reactor shown in FIG. 2.10268] The solutions used were a methylene chloridesolution of a mixture of 1 -(3-dimethylaminophenyl)ethanol (0.06 M) and dimethyl sulfide (0.13 M) with the adjusted concentrations (solution Al), a N-chlorosuccinimide/methylene chloride solution (0.09 M) (solution A2), a triethyl amine/methylene chloride solution (0.09 M) (solution A3), and a solution (0.18 M) prepared in such a method that the amount of a sodium hypochiorite aqueous solution (concentration 13.3%) became 2.0 molar equivalent based on the amount of N-chlorosuccinimide (solution B).10269] Pump LC-2OAT or LC-lOAi manufactured by SRIMADZU CORPORATION was used to feed the solutions Al, A2, A3, and B to the microreactot The solutions Al to A3 and B were supplied at a flow rate of 1.5 mE/mm to the microreactot In this process, the retention time at sections 12 to 14, 15 to 17, and 18 to 20 in the micromixer of FIG.2 were 10.5 seconds, 15.8 seconds, and 0.5 seconds, respectively. The diameter of the flow passage (the inner diameter of the micromixer) was 0.25 mm at sections 11 to 12, 13 to 12, 14 to 15, 16 to 15, 17 to 18, and 19 to 18, and immediately downstream of points 12, 15, and 18. The reaction temperature was -10° C. at sections 7 to 14 and 8 to 14, and 30° C. at sections 14 to 20, 9 to 20, and 10 to 20. Afier a waiting time of 3 minutes, the reaction liquid flowing out of the exit of the reactor was sampled for 15 seconds into a sampling tube containing 1 mE of pure water and then stirred at 25° C. for 10 seconds. The reaction solution was analyzed using RPLC, in which quantitative analysis was performed by internal standardization using a standard material. As a result, the total yield of the desired ketone compound (yield after the deodorization step) was 90%, and no influence of the oxidation reaction on the substrate was observed.
74%	With phosphotungstate-Fe³⁺ dual-metal-site modulated graphitic carbon nitride In acetonitrile at 25 - 35℃; for 20h; Sealed tube; Irradiation;
65%	With 12-molybdophosphoric acid; oxygen; Cu(OAc)₂*H₂O In lithium hydroxide monohydrate; acetonitrile at 90℃; for 8h;
62%	With dicarbonyl(cyclopentadienyl)iron(II) chloride; sodium hydride In toluene for 20h; Reflux; Inert atmosphere; Schlenk technique;
61%	In acetonitrile at 25℃; for 15h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;
58%	With C₁₉H₂₁CoINO; potassium-t-butoxide In propan-2-one at 80℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
51%	With Peroxyacetic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In acetonitrile at 20℃; for 12h;
40%	With tert.-butylhydroperoxide; Rh<SUB>2</SUB>(Msip)<SUB>4</SUB>; Sodium hydrogenocarbonate In dichloromethane; lithium hydroxide monohydrate at 40℃; for 24h; Sealed tube; chemoselective reaction;
35%	With tert.-butylhydroperoxide; tetra-n-butyl-ammonium chloride; anhydrous sodium carbonate In lithium hydroxide monohydrate at 40℃; for 24h;
20%	With tert.-butylhydroperoxide; Eosin In decane; acetonitrile at 25℃; for 72h; Inert atmosphere; Irradiation; Molecular sieve; Green chemistry; chemoselective reaction;	General procedure for oxidation of alcohols: General procedure: Oven dried round bottom flask was charged with Eosin Y (5 mmol) alcohol (1 mmol) and 3 equiv. of TBHP (5.5 M in decane) in dry ACN. The resulting mixture was degassed for 15 mins, followed by back filling N2, and then irradiated under Blue LED light (12W, 455 nm) at room temperature (25 oC). After reaction completion monitored through TLC, the mixture was diluted with 15 ml of 10% NaHCO3 solution, and extracted with EtOAc (3 × 20 ml). The combined organic extracts were washed with brine (20 ml), dried over Na2SO4, and concentrated on vacuo. Purification of the crude product on silica gel using EtOAc:Hexane as solvent system afforded the desired product.
46 % Chromat.	In N,N-dimethyl-formamide at 32℃; for 192h; Baker's yeast, pH 5 phosphate buffer;
	With oxygen; potassium carbonate In lithium hydroxide monohydrate at 20℃; for 24h;
	In para-xylene at 130℃; for 24h;
80 %Chromat.	With (trifluoromethyl)benzene; oxygen In lithium hydroxide monohydrate at 20℃; for 48h;
	With hydrotalcite supported Cu nanoparticles In para-xylene at 130℃; for 17h; Inert atmosphere;
58 %Chromat.	With (trifluoromethyl)benzene; lithium hydroxide monohydrate; oxygen; potassium carbonate at 30℃; for 48h;
45 %Chromat.	With Caswell No_. 744A; I,I-bischloroiodobenzene In acetonitrile at 0℃; for 48h;
100 %Chromat.	With ruthenium (III) chloride; oxone; 4-Jod-benzolsulfonsaeure In lithium hydroxide monohydrate; acetonitrile at 20℃; for 10h;
100 %Chromat.	With ruthenium (III) chloride; 4-iodobenzene; oxone In lithium hydroxide monohydrate; acetonitrile at 20℃; for 10h; Inert atmosphere;
60 %Chromat.	With lithium hydroxide monohydrate; oxygen at 50℃; for 12h; aq. buffer;
94 %Chromat.	With Caswell No_. 744A; [bis(acetoxy)iodo]benzene In acetonitrile at 6 - 10℃; for 24h; Inert atmosphere;
81 %Chromat.	With hydrotalcite-supported gold nanoparticles (Au/HT); air In toluene at 40℃; for 24h;
	With glucose dehydrogenase; D-glucose; (R)-specific alcohol dehydrogenase from Candida maris IFO₁₀₀₀₃; nicotinamide adenine dinucleotide In dimethyl sulfoxide aq. phosphate buffer; Enzymatic reaction;
81 %Spectr.	With oxygen In methanol at 60℃; for 22h;
	With 4.8 % platinum on carbon In 1,4-dioxane; lithium hydroxide monohydrate at 99.84℃; for 6h; Autoclave;
95 %Chromat.	With styrene; 2C₁₃H₈NS^(1-)C₁₂H₂₇PIr⁽³⁺⁾*CF₃O₃S^(1-); potassium-t-butoxide In toluene at 110℃; for 12h; Schlenk technique; Inert atmosphere;
	With silver⁽⁰⁾ nanoparticles supported on silica-coated ferrite In toluene for 24h; Inert atmosphere; Reflux;
	With gold nanoparticles; dihydrogen peroxide In methanol; lithium hydroxide monohydrate at 55℃; for 8h; Inert atmosphere; chemoselective reaction;	Catalytic reaction General procedure: The liquid-phase oxidation reactions were performed usinground bottom flask equipped with water condenser and a mag-netic stirrer. In a typical alcohol oxidation reaction, 0.67 g (5 mmol)of cinnamyl alcohol was mixed with 5 mL of methanol and 0.56 g(5 mmol) of dilute H2O2(30 wt% aqueous solution) in a 25 mL two-necked round bottom flask followed by addition of 5 wt% catalystwith respect to substrate. Cycloheptanone was used as an inter-nal standard to quantify the reaction product. The reaction wasperformed at 328 K while effectively circulation ice-cold waterthrough the condenser and the mixture was maintained under N2atmosphere using a N2balloon. The progress of the reaction wasmade by analyzing the products with a capillary gas chromato-graph (Agilent 13G, OV-1 column with flame ionization detector,FID). The quantification of products has been performed with spe-cial care using internal standard and response factor of reactantand products. For catalyst reusability study, the catalyst was recov-ered through centrifugation followed by activation under 5% H2(remaining N2) atmosphere at 180C. It is pertinent to mention thatlow-temperature activation was carried out to remove the physi-cally adsorbed organic reactant, product or solvent molecules fromthe metal surface of the used catalyst
	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; Trametes versicolor laccase In 2-methoxy-2-methylpropane at 30℃; for 16h; Enzymatic reaction;
	With silver nanoparticles immobilized onto poly(4-vinylpyridine)-functionalized Fe₃O₄ nanoparticles In toluene for 24h; Inert atmosphere; Reflux;
	With oxygen; 1-(tert-butylsulfonyl)-2-iodylbenzene at 70℃; for 14h;
	With sulfur(VI) fluoride; potassium carbonate; dimethyl sulfoxide at 20℃; for 12h; chemoselective reaction;
	With oxygen at 120℃; for 12h;	14 Example 14: (S)-1-(pyridin-2-yl)ethanol 0.5 mmol of 1-(pyridin-2-yl)ethanol was added to the test tube, 1.5 mmol of dipropylene glycol dimethyl ether was added to the oxygen balloon, and the reaction was completed at 120 ° C for 12 hours until the reaction was completed, and sodium formate 2.5 mmol was added to the reaction system. Then add 0.0025 mmol of catalyst B, add 4 mL of methanol:water (3:1), replace with nitrogen three times, react at 50 ° C for 12 h, wash with water after the reaction, extract the aqueous phase with ethyl acetate three times, and concentrate the organic phase to dry. Column chromatography (petroleum ether: ethyl acetate = 2:1) gave (S)-1-(pyridin-2-yl)ethanol (48.2 mg),yield of 79%, ee of 85%. HPLC separation conditions: chiral column contest OD-H column, mobile phase: n-hexane / isopropanol = 49:1 (volume ratio), flow rate: 0.5 ml / min, wavelength: 254 nm, temperature, 25 ° C, t1 = 14.63min, t2=15.58min;

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4
[ 1121-60-4 ]
[ 75-16-1 ]
[ 18728-61-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	In diethyl ether at 0℃; for 2h;
61%	In diethyl ether at 0 - 5℃; for 2h; Inert atmosphere;
	Yield given;

	In tetrahydrofuran at 0 - 20℃; for 4.25h; Inert atmosphere;
	In tetrahydrofuran at 0 - 20℃; for 4.25h; Inert atmosphere;	2-(1-Bromoethyl)pyridine (2t): General procedure: To a 0 °C solution of pyrimidine-2-carbaldehyde(2.5 g, 23.1 mmol) in THF (25 mL) under N2 was added ethyl magnesium bromide (0.5M in THF, 55 mL, 27.5 mmol) dropwise over 15 min. After stirring at 0 °C after 30 min, the mixture was allowed to warm with the ice bath to rt and stir at rt for 3.5 hr. The resulting reaction mixture was treated with saturated aqueous NH4Cl solution (15 mL) followed by water (35 mL), extracted with EtOAc (2 × 10 mL). The combined organic layers were dried over MgSO4.After removal of organic solvents, purification of the residue by flash chromatography on silica gel using 10-70% EtOAc/Hexanes as eluent provided the 1-(pyrimidin-2-yl)propan-1-ol as a colorless syrup (2.17 g, 68%)
	In tetrahydrofuran

Reference： [1]Uenishi, Jun'ichi; Hiraoka, Takao; Hata, Shinichiro; Nishiwaki, Kenji; Yonemitsu, Osamu; Nakamura, Kaoru; Tsukube, Hiroshi [Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2481 - 2487]
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5
1-(pyridine-2-yl)ethanol [ No CAS ]
[ 27911-63-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	With air; cells of Geotrichum candidum IFO 5767 In water at 30℃; for 24h;
	Multi-step reaction with 2 steps 1: Novozyme-435; molecular sieves 4A / diethyl ether / 5 h / 20 °C 2: 98 percent / K₂CO₃ / methanol
	Multi-step reaction with 2 steps 1: 82 percent / pyridine / 1 h / 20 °C 2: Candida rugosa lipase E_.⁽¹⁾C₃₁₁₃ type VII; aq. NaOH / aq. phosphate buffer / 7 h / 20 °C / pH 7.2

	Multi-step reaction with 2 steps 1: lipase Amano PS / benzene / 48 h / 35 °C 2: 71.6 percent / lipase Amano PS,potassium phosphate buffer / 12 h / 25 °C
	Multi-step reaction with 2 steps 1: 47 percent / molecular sieves 4A / diisopropyl ether / 4 h / Ambient temperature; Candida antarctica lipase presence
	Multi-step reaction with 2 steps 1: Candida antarctica lipase B / toluene / Resolution of racemate 2: lithium hydroxide; methanol / Inert atmosphere; Schlenk technique

Reference： [1]Nakamura, Kaoru; Fujii, Mikio; Ida, Yoshiteru [Tetrahedron Asymmetry, 2001, vol. 12, # 22, p. 3147 - 3153]
[2]Orrenius, Christian; Mattson, Anders; Norin, Torbjoern [Tetrahedron Asymmetry, 1994, vol. 5, # 7, p. 1363 - 1366]
[3]Brown, Dean G.; Urbanek, Rebecca A.; Bare, Thomas M.; McLaren, Frances M.; Horchler, Carey L.; Murphy, Megan; Steelman, Gary B.; Empfield, James R.; Forst, Janet M.; Herzog, Keith J.; Xiao, Wenhua; Dyroff, Martin C.; Lee, Chi-Ming C.; Trivedi, Shephali; Neilson, Kathy L.; Keith, Richard A. [Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3553 - 3556]
[4]Bellezza, Francesca; Cipiciani, Antonio; Cruciani, Gabriele; Fringuelli, Francesco [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 24, p. 4439 - 4444]
[5]Kawai, Yasushi; Hida, Kouichi; Ohno, Atsuyoshi [Bioorganic Chemistry, 1999, vol. 27, # 1, p. 3 - 19]
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6
[ 109-04-6 ]
[ CAS Unavailable ]
[ 18728-61-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 2-bromo-pyridine With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 2h; Stage #2: acetaldehyde at 20℃; for 2h;
79%	Stage #1: 2-bromo-pyridine With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 2h; Stage #2: acetaldehyde In tetrahydrofuran at 20℃; for 18h;

Reference： [1]Trecourt, Francois; Breton, Gilles; Bonnet, Veronique; Mongin, Florence; Marsais, Francis; Queguiner, Guy [Tetrahedron Letters, 1999, vol. 40, # 23, p. 4339 - 4342]
[2]Trécourt, François; Breton, Gilles; Bonnet, Véronique; Mongin, Florence; Marsais, Francis; Quéguiner, Guy [Tetrahedron, 2000, vol. 56, # 10, p. 1349 - 1360]

7
[ 18728-61-5 ]
[ 955885-20-8 ]
[ 955881-58-0 ]

Yield	Reaction Conditions	Operation in experiment
27%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	81 Example 81; 2,2-Dimethyl-4-(1-pyridin-2-yl-ethoxy)-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide; To a solution of 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (31a) (80 mg, 0.28 mmol) and 1-pyridin-2-yl-ethanol (81a) (48 mg, 0.39 mmol) in 4 mL of THF was added PPh3 (110 mg, 0.42 mmol) at 0° C., followed by DIAD (0.082 mL, 0.42 mmol) drop-wise. The mixture was stirred at room temperature overnight, concentrated, and purified by reverse phase HPLC to give a white solid (30 mg, 27% yield). 1H NMR (400 MHz, CDCl3) δ 9.61 (br. s., 1H) 8.79 (d, J=4.55 Hz, 1H) 7.94-8.06 (m, 1H) 7.69 (d, J=8.08 Hz, 1H) 7.45-7.53 (m, 1H) 7.27-7.31 (m, 1H) 6.94-7.00 (m, 2H) 6.81-6.86 (m, 1H) 5.84 (q, J=6.40 Hz, 1H) 3.80 (s, 3H) 3.09 (s, 2H) 1.70-1.77 (m, 3H) 1.48 (d, J=4.80 Hz, 6H); LCMS for C22H24N4O3 m/z 393.20 (M+H+).
27%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	81 Example 81:; 2,2-Dimethyl-4-(1-pyridin-2-yl-ethoxy)-2,3-dihydro-benzofuran-6-carboxylic acid (1- methyl-1 H-pyrazol-3-yl)-amide; To a solution of 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3- yl)-amide (31a) (80 mg, 0.28 mmol) and 1-pyridin-2-yl-ethanol (81a) (48 mg, 0.39 mmol) in 4 mL of THF was added PPh3 (110 mg, 0.42 mmol) at O0C, followed by DIAD (0.082 mL, 0.42 mmol) drop-wise. The mixture was stirred at room temperature overnight, concentrated, and purified by reverse phase HPLC to give a white solid (30 mg, 27% yield). 1H NMR (400 MHz, CDCI3) δ 9.61 (br. s., 1 H) 8.79 (d, J=4.55 Hz, 1 H) 7.94 - 8.06 (m, 1 H) 7.69 (d, .7=8.08 Hz, 1 H) 7.45 - 7.53 (m, 1 H) 7.27 - 7.31 (m, 1 H) 6.94 - 7.00 (m, 2 H) 6.81 - 6.86 (m, 1 H) 5.84 (q, J=6.40 Hz, 1 H) 3.80 (s, 3 H) 3.09 (s, 2 H) 1.70 - 1.77 (m, 3 H) 1.48 (d,J=4.80 Hz, 6 H); LCMS for C22H24N4O3 m/z 393.20 (M+H+). j

Reference： [1]Current Patent Assignee: PFIZER INC - US2008/280875, 2008, A1 Location in patent: Page/Page column 56
[2]Current Patent Assignee: PFIZER INC - WO2007/122482, 2007, A1 Location in patent: Page/Page column 77-78

8
[ 18728-61-5 ]
[ 124-63-0 ]
[ 780802-79-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In dichloromethane for 1.16667h;	240 EXAMPLE 240, COMPOUND 240: N1,N1-bis-(1-pyridin-2-yl-ethyl)-butane-1,4-diamine (HBr salt) EXAMPLE 240 COMPOUND 240: N1,N1-bis-(1-pyridin-2-yl-ethyl)-butane-1,4-diamine (HBr salt) To a stirred solution of 1-pyridin-2-yl-ethanol (156 mg, 1.27 mmol) (Mandal, S. K. et al. J Org Chem. 2003, 68, 4600-4603) and Et3N (0.27 mL, 1.94 mmol) in CH2Cl2 (5 mL) was added methanesulphonyl chloride (0.11 mL, 1.29 mmol) and the solution was stirred for 70 minutes. The solution was diluted with CH2Cl2 (20 mL) and washed with saturated aqueous NaHCO3 (215 mL) and brine (115 mL). The combined aqueous phase was extracted with CH2Cl2 (1*15 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated under reduced pressure to give crude methanesulphonic acid 1-pyridin-2-yl-ethyl ester as a yellow oil (269 mg, 100%). 1H NMR (CDCl3) δ 1.77 (d, 3H, J=6.6 Hz), 2.94 (s, 3H), 5.79 (q, 1H, J=6.6 Hz), 7.28 (ddd, 1H, J=7.4, 7.1, 1.3 Hz), 7.47 (d, 1H, J=7.9 Hz), 7.76 (td, 1H, J=7.6, 1.7 Hz), 8.61 (d, 1H, J=4.9 Hz).
96%	With dmap In dichloromethane at 0 - 20℃;
	With triethylamine In dichloromethane at 18 - 25℃;	110.110a In a 100 mL round-bottomed flask was dissolved l-(pyridin-2-yl)ethanol (0.90 g, 7.31 mmol), TEA (1.528 mL, 10.96 mmol), and DMAP (0.045 g, 0.37 mmol) in DCM (20 mL) to give a colorless solution. Methanesulfonyl chloride (0.598 mL, 7.67 mmol) was added and the reaction was stirred at RT overnight. The solution was washed with water (20 mL) and the organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by ISCO MPLC (0-5% MeOH in DCM) to give l-(pyridin-2-yl)ethyl methanesulfonate. To the product was added methyl 4-hydroxybenzoate (0.867 g, 5.70 mmol) and K2CO3 (2.148 g, 15.55 mmol) in MeCN (50 mL) to give a white suspension. The reaction was heated to 85 0C and stirred for 2h. After concentration in vacuo, the residue was diluted with water (20 mL) and DCM (30 mL). The aqueous layer was extracted with DCM (2 X 15 mL) and the combined organic layers were dried (Na2SO4), and concentrated in vacuo to give the crude product which was purified by ISCO MPLC (0-5% MeOH/DCM) to afford the title compound. 1R NMR (DMSO-d6) δ 1.62 (d, 3 H), 3.78 (s, 3 H), 5.59 (q, 1 H), 7.01 (d, 2 H), 7.31 (dd, 1 H), 7.43 (d, 1 H), 7.81 (m, 3 H), 8.57 (d, 1 H).

	With triethylamine In dichloromethane at 0℃; for 0.5h;	50 tert-Butyl 4-(1-(pyridin-2-yl)ethyl)piperazine-1-carboxylate A solution of the alcohol 1-(pyridin-2-yl)ethanol (prepared following the procedure described in J. Chem. Soc., Perkin Trans. 1, 2000, 4439-4444) (100 mg, 0.81 mmol) in CH2Cl2 (4 mL) at 0° C. was treated with triethylamine (5.0 eq, 4.05 mmol, 0.56 mL) and MsCl (2.0 eq, 1.62 mmol, 0.13 mL) and stirred at 0° C. for 30 minutes. It was then washed with water, brine, dried (MgSO4) and concentrated in vacuo to give the crude mesylate. This was immediately redissolved in DMSO (3 mL) at room temperature, treated with N-BOC piperazine (4.0 eq, 3.24 mmol, 605 mg) and stirred at 60° C. for 18 h. After this time, the mixture was poured into water and extracted with EtOAc (2×10 mL) and CHCl3 (2×10 mL). The combined extracts were dried (MgSO4), concentrated in vacuo and purified by column chromatography (EtOAc) to give the product (161 mg, 68% for two steps) as a colourless oil; 1H-NMR (500 MHz, CDCl3) 1.46 (s, 9H, C(CH3)3), 1.65 (br s, 3H, CHCH3), 2.34-2.58 (m, 4H, piperazine N(CH2)2), 3.48-3.62 (m, 5H, CHCH3 & piperazine N(CH2)2), 7.18 (br s, 1H, pyridine H-3 or H-5), 7.40 (br s, 1H, pyridine H-3 or H-5), 7.68 (br s, 1H, pyridine H-4), 8.58 (br s, 1H, pyridine H-6);LC (Method B)-MS (ESI, m/z): Rt=2.07 min-292 [(M+H)+, 100%).
	With triethylamine In dichloromethane for 0.5h; Inert atmosphere; Cooling with ice;	G20 Example G20. General experimental for conversion of an alcohol to the corresponding mesylateGeneral Scheme:Representative SchemeTo a stirred solution of the alcohol starting material (e.g., l-(pyridin-2-yl)ethanol, 4.1 mmol) and Et3N (1.1 mL) in CH2C12 was added MsCl (0.5 mL) under N2 in ice bath. The mixture was stirred at the same temperature until the reaction was complete (approximately 0.5 h). The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic layers were dried over Na2S04 and concentrated under reduced pressure to yield the crude mesylate product (e.g., l-(pyridin-2-yl)ethyl methanesulfonate, 1.1 g).
7.8 g	With triethylamine In dichloromethane at 20℃; for 4h; Cooling with ice;	14.2 To an ice-cooled solution of 1-(pyridin-2-yl)ethanol (5.1 g) in DCM (80 mL) was added TEA (1 1.5 mL) followed by MsCI (3.5 mL). The reaction mixture was stirred at RT for 4 hours. Water (100 mL) was added. The organic layer was separated, dried over sodium sulfate and filtered. The filtrate was concentrated to afford 1 -(pyridin-2-yl)ethyl methanesulfonate (7.8 g) as a yellow liquid oil. MS(ES+) m/z 202 (MH+).

Reference： [1]Current Patent Assignee: SANOFI - US2004/209921, 2004, A1 Location in patent: Page 113
[2]Ghorai, Prasanta; Kraus, Anja; Keller, Max; Götte, Carsten; Igel, Patrick; Schneider, Erich; Schnell, David; Bernhardt, Günther; Dove, Stefan; Zabel, Manfred; Elz, Sigurd; Seifert, Roland; Buschauer, Armin [Journal of Medicinal Chemistry, 2008, vol. 51, # 22, p. 7193 - 7204]
[3]Current Patent Assignee: ASTRAZENECA PLC - WO2009/27746, 2009, A1 Location in patent: Page/Page column 99
[4]Current Patent Assignee: UNIVERSITY OF LONDON - US2009/247507, 2009, A1 Location in patent: Page/Page column 35
[5]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Pharma (in: Sumitomo Chemical) - WO2012/170845, 2012, A2 Location in patent: Page/Page column 113-114
[6]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2015/181186, 2015, A1 Location in patent: Page/Page column 54

9
[ 1122-62-9 ]
[ 20988-55-0 ]
[ 42088-91-5 ]

Yield	Reaction Conditions	Operation in experiment
	With C7H7O3PolS; sodium cyanoborohydride; ammonium chloride; In methanol; at 25℃; for 65h;	To a mixture ofl-pyridin-2-yl-ethanone (0.20 g, 1.65 mmol) and ammonium choride (0.88 g, 16.5 mmol) inMeOH (5 ml) was added sodium cyanoborohydride (0.125 g, 1. 98 mmol). The reaction was stirred at25 C for 64 hours and quenched by addition macroporous polystyrene sulfonic acid(MP-TsOH) (4. 08 g, 16.5 mmol) resin. The suspension was agitated for 1 hour. The resin was collected by filtration and washed withMeOH (3 x 20 ml, 20 minute shaking per wash). The resulted resin was then treated with NH3/MeOH solution (7 M, 15 ml) for 20 minutes, filtered, and washed withMeOH(2 x 15 ml). The combined filtrate was concentrated until the crude weighed 200 mg. The crude product contained about 30% desired product,35% alcohol, and 35% dimmer as indicated by LC/MS, and was directly used without further purification.

Reference： [1]Patent: WO2005/49033,2005,A1 .Location in patent: Page/Page column 98

10
[ 18728-61-5 ]
[ 857355-21-6 ]
[ 857354-99-5 ]

Yield	Reaction Conditions	Operation in experiment
11%	With PS-triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃; for 17h;	24 Example 24; N-cyclopropyl-4-methyl-3-{ [4-(1-pyridin-2-ylethoxy) benzoyl] amino} benzamide To 3-[4-(hydroxy)benzoyl]amino}-N-cyclopropyl-4-methylbenzamide (150 mg, 0. 484 mmol) in DCM (20 mL) was added polymer supported triphenyl phosphine (937 mg, 1.45 mmol) and the 1-pyridin-2-ylethanol (45 mg, 0.363 mmol). Diethyl azodicarboxylate (126 mg, 0.726 mmol) was then added dropwise. The reaction was stirred for 17 h at room temperature and was then filtered and the filtrates were evaporated. The crude residue was purified by flash silica chromatography using ethyl acetate in iso-hexane (5-100%) as the eluent to give the title compound as a colourless oil (22 mg, 11%) ; NMR Spectrum : (DMSOd6) 0.55 (m, 2H), 0. 68 (m, 2H), 1.64 (d, 3H), 2.22 (s, 3H), 2.83 (m, 1H), 5.60 (q, 1H), 7.02 (d, 2H), 7.31 (d, 2H), 7.43 (d, 1H), 7.62 (d, 1H), 7.80 (m, 2H), 7.90 (d, 2H), 8. 35 (d, 1H), 8. 58 (d, 1H), 9.75 (s, 1H) ; Mass Spectrum: M+H+ 416.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2005/61465, 2005, A1 Location in patent: Page/Page column 64

11
[ 18728-61-5 ]
[ 357286-82-9 ]
[ 357287-34-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,2-dimethoxyethane	279 (RS)-2-Amino-4-(5-methyl-furan-2-yl)-6-(1-pyridin-2-yl-ethoxy)-pyrimidine-5-carbonitrile Example 279 (RS)-2-Amino-4-(5-methyl-furan-2-yl)-6-(1-pyridin-2-yl-ethoxy)-pyrimidine-5-carbonitrile From 2-amino-4-(5-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile, (RS)-alpha-methyl-2-pyridinemethanol and DBU in DME. ES-MS m/e (%): 344 (M+Na+, 20), 322 (M+H+, 100).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2001/27196, 2001, A1

12
[ 18728-61-5 ]
[ 357286-73-8 ]
[ 357286-89-6 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,2-dimethoxyethane	242 (RS)-2-Amino-4-furan-2-yl-6-(1-pyridin-2-yl-ethoxy)-pyrimidine-5-carbonitrile Example 242 (RS)-2-Amino-4-furan-2-yl-6-(1-pyridin-2-yl-ethoxy)-pyrimidine-5-carbonitrile From 2-amino-4-furan-2-yl-6-methanesulfinyl-pyrimidine-5-carbonitrile, (RS)-alpha-methyl-2-pyridinemethanol and DBU in DME. ES-MS m/e (%): 308 (M+H+, 100).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2001/27196, 2001, A1

13
1-(pyridine-2-yl)ethanol [ No CAS ]
HBr (conc) [ No CAS ]
rapamycin 42-ester [ No CAS ]
[ 75504-01-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		5 Rapamycin 42-ester with 2,2-dimethyl-4-(2-pyridinyl) butyric acid EXAMPLE 5 Rapamycin 42-ester with 2,2-dimethyl-4-(2-pyridinyl) butyric acid To 2-(hydroxyethyl)pyridine (10 mL, 88.8 mmol) was added HBr (conc) (90 mL). The mixture was heated to reflux overnight. The next day, excess HBr was removed and the resulting solid recrystallized from iPrOH to provide 2-(bromoethyl)pyridine, yield=100%. 1 H NMR (300 MHz, DMSO) δ3.0 (t, 2H), 3.9 (t, 2H), 7.79 (t, 1H), 7.8 (d, 1H), 8.4 (t, 1H), 8.7 (d, 1H).

Reference： [1]Current Patent Assignee: PFIZER INC - US5385908, 1995, A

14
[ 18728-61-5 ]
[ 74-88-4 ]
[ 23950-22-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	With sodium hydride In mineral oil at 0 - 20℃; Inert atmosphere;
	In dimethyl sulfoxide	26 EXAMPLE 26 To a stirred solution of 223 g. of 1-(2-pyridyl)-ethanol in 1500 ml. of dry dimethylsulfoxide is added 2.3 moles of sodium hydride in portions, under nitrogen, maintaining the temperature at 20°C. After two hours, 331 g. of methyl iodide is added at 20°C. After stirring for another 3 hours, the mixture is poured onto ice-water and extracted three times with ether. The organic phase is washed with water, dried over magnesium sulfate, concentrated in vacuo, and the residue is distilled to give 2-(1-methoxyethyl)pyridine.

Reference： [1]Balakrishnan, Venkadesh; Murugesan, Vetrivelan; Chindan, Bincy; Rasappan, Ramesh [Organic Letters, 2021, vol. 23, # 4, p. 1333 - 1338]
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - US3966945, 1976, A

15
[ 18728-61-5 ]
[ 120-47-8 ]
[ 869108-48-5 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 3h;	11.2 Production Example 11-2: Ethyl 4-(1-pyridin-2-ylethoxy)benzenecarboxylate: Triphenyl phosphine (5.1 g) and a THF solution (5 mL) of diisopropyl azodicarboxylate (3.9 mL) were added in that order a THF solution (40 mL) of the compound (2.0 g) obtained in Production Example 11-1 and ethyl 4-hydroxybenzenecarboxylate (2.7 g), and stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate = 9/1 to 3/2) to obtain the entitled compound (4.4 g).

Reference： [1]Current Patent Assignee: MERCK & CO INC - EP1748048, 2007, A1 Location in patent: Page/Page column 38

16
[ 18728-61-5 ]
[ 1025772-34-2 ]
[ 1025771-59-8 ]

Yield	Reaction Conditions	Operation in experiment
38%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 10h;	20 Synthesis of (1R)-N-(4-chloro-3-(1-(pyridin-2-yl)ethoxy)benzyl)-1-(3-chlorophenyl)ethanamine EXAMPLE 20 Synthesis of (1R)-N-(4-chloro-3-(1-(pyridin-2-yl)ethoxy)benzyl)-1-(3-chlorophenyl)ethanamine To a solution of (R)-2-chloro-5-((1-(3-chlorophenyl)ethylamino)methyl)phenol 96 (130 mg, 439 μmol) in 5 mL of THF under N2 was added triphenylphosphine (127 mg, 483 μmol). The solution was chilled to 0° C. in an ice bath and then diisopropyl azodicarboxylate (94 μL, 483 μmol) was added dropwise to the reaction. After stirring for 15 min 0° C., a solution of 1-(pyridin-2-yl)ethanol (59 mg, 483 μmol) in THF was added to the reaction. The reaction was allowed to warm to room temperature and it was stirred for 10 h. The reaction was concentrated and diluted with EtOAc. The solution was extracted with saturated NaHCO3, water, and then brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography using a 5% to 90% gradient of EtOAc in hexanes as the eluant. The desired fractions were combined and concentrated to give (1R)-N-(4-chloro-3-(1-(pyridin-2-yl)ethoxy)benzyl)-1-(3-chlorophenyl)ethanamine 98 (67 mg, 38% yield) as a colorless oil and as a mixture of diastereomers. 1H NMR (400 MHz, d4-methanol) δ ppm 1.60 (d, J=6.65 Hz, 2.1H) 1.73 (d, J=5.28 Hz, 3H) 1.83 (d, J=6.46 Hz, 3H) 3.90 (d, J=11.15 Hz, 1H) 4.16 (d, J=12.72 Hz, 1H) 4.45-4.54 (m, 1H) 5.18-5.28 (m, 0.7H) 5.99 (m, 1H) 7.05 (d, 1H) 7.48 (m, 5H) 7.63 (m, 1H) 7.99 (m, 1.7H) 8.08 (m, 0.7H) 8.20 (d, 1H) 8.59 (m, 1.7H) 8.73 (m, 0.7H) 8.83 (d, 1H). Mass spectrum: calculated for C22H22Cl2N2O 401.3; found 402.4 (M++1).

Reference： [1]Current Patent Assignee: AMGEN INC - US2008/221101, 2008, A1 Location in patent: Page/Page column 42

17
[ 18728-61-5 ]
[ 1897-52-5 ]
[ 872180-98-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-(pyridine-2-yl)ethanol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.5h; Stage #2: 2,6 difluorobenzonitrile In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 72h;	57.2 Step 2; Sodium hydride (60%; 37 mg; 0.92 mmol) was suspended in DMF and cooled to 0 °C under inert atmosphere. The previous alcohol (113 mg; 0.92 mmol) in DMF was added dropwise to the sodium hydride mixture. The solution was allowed to warm to room temperature and stirred for 30 minutes. The solution was then added dropwise to a solution of 2,6-difluorobenzonitrile (127 mg; 0.92 mmol) in DMF cooled to 0 °C. The mixture was allowed to warm to room temperature and stirred for 72 hours. The solution was poured over water and extracted with ethyl acetate and solvent removed. Purification by column chromatography (methanol / dichloromethane) yielded 184 milligrams of 2-fluoro-6-(I-pyridin-2- ylethoxy) benzonitrile.

Reference： [1]Current Patent Assignee: FAMILIES OF SPINAL MUSCULAR ATROPHY - WO2005/123724, 2005, A1 Location in patent: Page/Page column 46

18
[ 18728-61-5 ]
[ 38186-88-8 ]
[ 1351763-45-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran; mineral oil at 70℃; for 16h; Inert atmosphere;	5-Fluoro-2-(l-(pyridin-2-yl)ethoxy)nicotinic acid (21p)To a solution of 2-chloro-5-fluoronicotinic acid (1. lg, 6.3mmol) in THF (15ml) under a N2 atmosphere was added 1 -(pyridin-2-yl)ethanol (l .Og, 8.8mmol) followed by a portion-wise addition of NaH (60% dispersion in mineral oil, 0.75g, 19mmol). The resulting suspension was stirred at 70°C for 16h and then cooled to room temperature and quenched with 1M NaOH (10ml). After washing with DCM (x2), the aqueous layer was acidified with concentrated HCl until the solution was ~pH5. The products were extracted into EtOAc (x2) and dried to afford the title compound as a dark brown oil.NMR δ 8.53 (IH, ddd, J4.8, 1.7, 1.0), 8.29 (IH, d, J 3.2), 8.04 (IH, dd, J 8.2, 3.2), 7.80 (IH, td, J 7.7, 1.7), 7.56 (IH, d, J 7.9), 7.29 (IH, ddd, J7.5, 4.5, 1.0), 6.21 (IH, q, J 6.6), 1.61 (3H, d, J 6.6);MS (m/e) 263 [M+H]+, Rt 0.55min (QC Method 1)

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2011/151651, 2011, A1 Location in patent: Page/Page column 69-70

19
[ 18728-61-5 ]
[ 122-79-2 ]
[ 113625-58-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With (1,2,3,4,5-pentamethylcyclopentadienyl)Ir-[κ²(N,C)-(NHC(CH₃₎₂-2-C₆H₄)] In toluene at 30℃; for 12h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;

Reference： [1]Sato, Yasuhiro; Kayaki, Yoshihito; Ikariya, Takao [Chemical Communications, 2012, vol. 48, # 30, p. 3635 - 3637]

20
[ 74115-13-2 ]
[ 18728-61-5 ]
[ 1610521-03-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With cyanomethylenetributyl-phosphorane In toluene at 120℃; for 0.666667h; Microwave irradiation; Sealed tube; Overall yield = 80 %; Overall yield = 154.6 mg;	89 Intermediate 89: (S)-3-bromo-5-(1-(pyridin-2-yl)ethoxy)pyridine A mixture of (R)-1-(pyridin-2-yl)ethanol (107.3 mg, 0.871 mmol), 5-bromopyridin-3-ol (120.9 mg, 0.695 mmol) and 2-(tributylphosphoranylidene)acetonitrile (501.2 mg, 2.077 mmol) in toluene (3 mL) was heated with stirring in a sealed vial in a microwave reactor at 120 °C for 40 min. The mixture was concentrated under a stream of nitrogen and the residue was re-dissolved in DCM (~3 mL) and was purified by Biotage SP4 flash column chromatography (10g silica SNAP cartridge) eluting with a gradient of 0-8% (2M ammonia in MeOH solution) in DCM. The required fractions were combined and the solvent evaporated under a stream of nitrogen to give the crude desired product which was further purified by Biotage SP4 flash column chromatography (10g silica SNAP cartridge) eluting with a gradient of 0-50% EtOAc in cyclohexane. The required fractions were combined and the solvent evaporated in vacuo to give the title compound as an orange oil (154.6 mg, 0.554 mmol, 80 % yield) LCMS (2 min, Formic Acid): Rt = 0.83 min, MH+ = 279/281 Enantiomeric purity by chiral HPLC = >86% e.e.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/78257, 2014, A1 Location in patent: Page/Page column 112; 113

21
[ 74115-13-2 ]
[ 18728-61-5 ]
[ 1610520-31-4 ]

Yield	Reaction Conditions	Operation in experiment
52.2%	With cyanomethylenetributyl-phosphorane In toluene at 120℃; for 1h; Microwave irradiation; Sealed tube;	6 Intermediate 6: (±)-3-bromo-5-(1-(pyridin-2-yl)ethoxy)pyridine A mixture of (±)-1-(pyridin-2-yl)ethanol (100.5 mg, 0.816 mmol), 5-bromopyridin-3-ol (283.2 mg, 1.628 mmol) and 2-(tributylphosphoranylidene)acetonitrile (595.0 mg, 2.465 mmol) in toluene (3 mL) were heated with stirring in a sealed vial in a microwave reactor at 120 °C for 60 min. The mixture was concentrated under a stream of nitrogen and the residue was purified by column chromatography on silica gel eluting with a gradient of 0-50% ethyl acetate in cyclohexane. The required fractions were combined and evaporated in vacuo to give the desired product but contaminated with some of the starting 5-bromopyridin-3-ol. This residue was repurified by chromatography on silica gel eluting with a gradient of 0-8% (2M ammonia in methanol solution) in dichloromethane. The required fractions were combined and the solvent evaporated under a stream of nitrogen to give the desired product (±)-3-bromo-5-(1-(pyridin-2-yl)ethoxy)pyridine (1 18.9 mg, 0.426 mmol, 52.2% yield) as a brown oil. LCMS (2 min, Formic Acid): Rt = 0.83 min, MH+ = 279/281.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/78257, 2014, A1 Location in patent: Page/Page column 73; 74

22
[ 18728-61-5 ]
[ 503173-07-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With trimethylsilylazide; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 30℃; for 0.333333h;	General Procedure for Azidation General procedure: To a stirred solution of alcohol 1 (1.0 mmol) and azidotrimethylsilane(TMSN3; 1.5 mmol) in CH2Cl2 (2.0 mL) was added Cu(OTf)2(5 mol%), and the reaction mixture was stirred at r.t. (ca. 30 °C) for 20 min. On completion of the reaction as indicated by TLC, the reactionwas diluted with H2O and extracted with EtOAc. The organiclayers were dried with anhydrous Na2SO4, filtered, and evaporatedunder vacuum. The crude residue was purified by column chromatography(60-120 mesh silica gel, 1:9; EtOAc-hexane).
84%	With [Bmim]Cl-ZnCl₂; trimethylsilylazide In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; Green chemistry;	General procedure for the synthesis of azides from alcohols (2) General procedure: A mixture of alcohol (1.0 mmol), trimethylsilylazide (1.1 mmol), [bmim]ZnCl3 (5 mol%) and dry DCM (3 mL) was placed in a 50 mL round-bottomed flask under nitrogen atmosphere. The reaction contents were stirred magnetically at room temperature for appropriate time as mentioned in Table 2. The progress of the reaction was monitored by TLC (eluent: ethylacetate: petroleum ether, 10:90, v/v). After completion of the reaction as indicated by TLC, it was quenched with water (5 mL). The reaction mixture was extracted with DCM (3 × 5 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered, and the solvent removed under vacuum to get crude product, which was purified by column chromatography using (eluent: ethyl acetate: petroleum ether, 1:99, v/v) to give corresponding product in good yield as mentioned in Table 2.

Reference： [1]Khedar, Poonam; Pericherla, Kasiviswanadharaju; Kumar, Anil [Synlett, 2014, vol. 25, # 4, p. 515 - 518]
[2]Singh, Ashima; Singh, Harjinder; Khurana [Tetrahedron Letters, 2017, vol. 58, # 25, p. 2498 - 2502]

23
1-(pyridine-2-yl)ethanol [ No CAS ]
[ 75504-01-7 ]

Yield	Reaction Conditions	Operation in experiment
33%	With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 0.45h; Inert atmosphere;	2-(1-Bromoethyl)pyridine (2t): General procedure: To a 0 °C mixture of 1-(pyrimidin-2-yl)propan-1-ol (1.1 g, 8.0 mmol) and triphenylphosphine (3.8 g, 14.6 mmol) in THF (55 mL) under N2 atmosphere was added perbromomethane (3.8 g,12.2 mmol). After stirring at 0 °C for 2 min, the mixture was allowed to warm to rt and stir for 25 min. The precipitate was filtered off through a pad of celite, the solid was wash with cold THF (10 mL). The solution was collected. After removal of the organic solvent under reduced pressure, purification of the residue by flash chromatography on silica gel with 0-5-15% EtOAc/Hexanes provided the title compound 2g as colorless oil.
	With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 0.45h; Inert atmosphere;

Reference： [1]Yu, Ming; Stevenson, Karis; Zhou, Gene [Tetrahedron Letters, 2014, vol. 55, # 41, p. 5591 - 5594]
[2]Yu, Ming; Wang, Yingcai; Zhu, Jiang; Bartberger, Michael D.; Canon, Jude; Chen, Ada; Chow, David; Eksterowicz, John; Fox, Brian; Fu, Jiasheng; Gribble, Michael; Huang, Xin; Li, Zhihong; Liu, Jiwen; Lo, Mei-Chu; McMinn, Dustin; Oliner, Jonathan D.; Osgood, Tao; Rew, Yosup; Saiki, Anne Y.; Shaffer, Paul; Yan, Xuelei; Ye, Qiuping; Yu, Dongyin; Zhao, Xiaoning; Zhou, Jing; Olson, Steven H.; Medina, Julio C.; Sun, Daqing [ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 894 - 899]

24
[ 18728-61-5 ]
[ 1799726-65-0 ]
[ 1799726-67-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate In toluene at 20℃; for 48h;	Intermediate 12: Methyl 3-(5-chloro-2-oxo-6-(1-(pyridin-2-yl)ethoxy)benzo[d]oxazol- 3(2H)-yl)propanoate Intermediate 12: Methyl 3-(5-chloro-2-oxo-6-(1-(pyridin-2-yl)ethoxy)benzo[d]oxazol- 3(2H)-yl)propanoate 1 -(Pyridin-2-yl)ethanol (71 mg, 0.57 mmol), diethyl azodicarboxylate (84 mg, 0.48 mmol) and triphenyphosphine (126 mg, 0.48 mmol) were added to methyl 3-(5- chloro-6-hydroxy-2-oxobenzo[d]oxazol-3(2H)-yl)propanoate (Intermediate 1 1 , 0.13 g, 0.48 mmol) in toluene (10 mL) and the reaction was stirred at room temperature for 2 days. The reaction mixture was poured into water (15 mL), aqueous layer was extracted with ethyl acetate (10 mL x 3), combined organic layer and dried over sodium sulphate and partially purified by column chromatography [silica: 200 - 300 mesh, 10 g] eluting with petroleum ether/ethyl acetate=4:1] to give methyl 3-(5- chloro-2-oxo-6-(1-(pyridin-2-yl)ethoxy)benzo[d]oxazol-3(2H)-yl)propanoate as a white solid (270 mg, crude). LCMS (A): Rt 1.57 min, MH+ 377.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF EDINBURGH - WO2015/91647, 2015, A1 Location in patent: Page/Page column 44

25
[ 18728-61-5 ]
[ 10445-92-8 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In dichloromethane at 20℃; for 2h; Cooling with ice;	1.2 Step 2: Synthesis of 2-(1-chloroethyl)pyridine. To an ice-cooled solution of 1-(pyridin-2-yl)ethanol (4.5 g, 36 mmol) in dry dichloromethane (100 mL) was slowly added thionyl dichloride (20 mL). The mixture was then warmed to 20 °C. After 2 h, the reaction was concentrated in vacuo, and the resulting residue was diluted with water (40 mL) and dichloromethane (60 mL). The solution wasneutralized with saturated aqueous sodium carbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution (3 x 30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford crude 2- (1 -chloroethyl)pyridine (5.0 g, 97% yield). The product was used without further purification.
	With thionyl chloride In dichloromethane at 20℃; for 2h; Cooling with ice; Inert atmosphere;	1.2 Synthesis of 2-(1-chloroethyl)pyridine To an ice-cooled solution of 1-(pyridin-2-yl)ethanol (4.5 g, 36 mmol) in dry dichloromethane (100 mL) was slowly added thionyl dichloride (20 mL). The mixture was then warmed to 20° C. After 2 h, the reaction was concentrated in vacuo, and the resulting residue was diluted with water (40 mL) and dichloromethane (60 mL). The solution was neutralized with saturated aqueous sodium carbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution (3*30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford crude 2-(1-chloroethyl)pyridine (5.0 g, 97% yield). The product was used without further purification.
	With thionyl chloride In dichloromethane

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2015/91889, 2015, A1 Location in patent: Page/Page column 79; 80
[2]Current Patent Assignee: ROCHE HOLDING AG - US2015/175619, 2015, A1 Location in patent: Paragraph 0249; 0250
[3]Magubane, Makhosazane N.; Alam, Mohd Gulfam; Ojwach, Stephen O.; Munro, Orde Q. [Journal of Molecular Structure, 2017, vol. 1135, p. 197 - 201]

26
[ 20988-55-0 ]
[ 23612-57-9 ]
7-(pyridin-2-yl)-1,2,3,4-tetrahydro-1,8-naphthyridine [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4054 - 4057

27
[ 18728-61-5 ]
[ CAS Unavailable ]
[ 54313-73-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With Cp*IrCl[κ₂(N,C)-{NH₂C-(C₆H₅)₂-2-C₆H₄}]; potassium-t-butoxide; pentan-3-one In tert-Amyl alcohol at 23℃; for 72h; Inert atmosphere;
80%	With C₁₇H₁₅Cl₃N₅Ru; potassium hydroxide at 110℃; for 6h; Inert atmosphere; Sealed tube; Green chemistry;
	With C₂₁H₁₈MnN₅O₄; potassium-t-butoxide In o-dimethylbenzene at 140℃; for 48h; Inert atmosphere;

26 %Spectr.	With (<SUP>Ph₂</SUP>NNN)NiCl<SUB>2</SUB>(CH<SUB>3</SUB>CN); sodium tertiary butoxide In neat (no solvent) at 140℃; for 24h; Glovebox; Inert atmosphere;
21 %Spectr.	With cobalt(II) chloride; sodium tertiary butoxide at 140℃; for 24h;
45 %Spectr.	With chromium(III) chloride hexahydrate; sodium tertiary butoxide at 140℃; for 24h;

Reference： [1]Lau, Kai Kiat; Liao, Gang; Ng, Teng Wei; Pan, Hui-Jie; Zhao, Yu [Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11384 - 11389][Angew. Chem., 2020, vol. 132, # 28, p. 11480 - 11485,6]
[2]Wang, Qingfu; Wu, Kaikai; Yu, Zhengkun [Organometallics, 2016, vol. 35, # 9, p. 1251 - 1256]
[3]Liu, Tingting; Wang, Liandi; Wu, Kaikai; Yu, Zhengkun [ACS Catalysis, 2018, vol. 8, # 8, p. 7201 - 7207]
[4]Arora, Vinay; Narjinari, Himani; Kumar, Akshai [Organometallics, 2021, vol. 40, # 16, p. 2870 - 2880]
[5]Kumar, Akshai; Kumar, Pradhuman; Nandi, Pran Gobinda [Catalysis science and technology, 2022, vol. 12, # 4, p. 1100 - 1108]
[6]Narjinari, Himani; Tanwar, Niharika; Kathuria, Lakshay; Jasra, Raksh Vir; Kumar, Akshai [Catalysis science and technology, 2022, vol. 12, # 15, p. 4753 - 4762]

28
1-(pyridine-2-yl)ethanol [ No CAS ]
[ 98-98-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With 1,10-Phenanthroline; oxygen; copper diacetate; potassium hydroxide In dimethyl sulfoxide at 130℃; for 12h; Autoclave;	2.2. Catalytic tests General procedure: The catalytic reactions were performed in a 10-mL autoclave reactor with an internal Teflon insert. Typically, 0.5 mmol of secondary alcohols, 0.04 mmol of Cu(OAc)2 and 0.04 mmol of ligand, 1 mmol of base, and 2 mL of solvent were added to the reactor.Then, the reactor was charged with 0.4 MPa O2 and heated to the desired temperature under magnetic stirring. When the reaction reached completion, the reaction mixture was diluted with 4 mL of methanol, and the catalyst was separated via centrifugation.The acid product was esterified with addition of 40 μl of BF3OEt2 at 100 °C for 6 h in Ar atmosphere. In reaction condition optimization experiment, the products were identified and quantified using gas chromatography-mass spectrometry (GC-MS) and an Agilent7890A/5975C instrument equipped with an HP-5 MS column (30 m in length, 0.25 mm in diameter). p-Xylene was used as the internal standard. In the substrate scope experiment, the product was isolated and identified by NMR. The procedure for the isolation of the product is as follows: after the reaction completed, the reactor was cooled to room temperature in water and vented the gas.The reaction mixture was acidified with HCl 1.0 M (pH 1-2,15 mL) and then extracted with Et2O (3 x 20 mL). Next, the combined organic layers were washed with HCl 1.0 M (pH 1-2,3 10 mL), dried over anhydrous Na2SO4, and filtered and the Et2O was rotary evaporated. Solid products obtained were vacuum dried for 10 h at 60 °C.

Reference： [1]Wang, Min; Lu, Jianmin; Li, Lihua; Li, Hongji; Liu, Huifang; Wang, Feng [Journal of Catalysis, 2017, vol. 348, p. 160 - 167]

29
[ 5344-90-1 ]
[ 18728-61-5 ]
[ 7491-86-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With C₃₁H₂₉NO₃P₂Re⁽¹⁺⁾*Br^(1-); potassium-t-butoxide In toluene at 150℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique;
91%	With potassium-t-butoxide; C₂₀H₁₉Cl₃N₇Ru In toluene at 120℃; for 6h; Green chemistry;
90%	With caesium hydroxide monohydrate; C₁₇H₁₄Br₂CoN₄ In toluene at 150℃; for 6h; Sealed tube; Inert atmosphere;

89%	With tetrabutylammonium bromide; potassium hydroxide In lithium hydroxide monohydrate at 100℃; for 12h; Green chemistry;
86%	With C₁₅H₉BrMnN₃O₃; potassium-t-butoxide In toluene at 110℃; for 12h; Inert atmosphere; Green chemistry;
80%	With nickel(II) dibenzotetramethyltetraaza[14]annulene; potassium-t-butoxide In toluene at 90℃; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;
78%	With bis(3,5-di-(tert-butyl)-2-hydroxyazobenzolato)nickel(II); potassium-t-butoxide; oxygen In toluene at 80℃; for 8h; Sealed tube;
78%	With 9,10-phenanthrenequinone; dimethyl sulfoxide; sodium hydroxide at 20℃; for 6h; Irradiation;
77%	With C₂₂H₂₄ClIrN₃O⁽¹⁺⁾*Cl^(1-); potassium hydroxide In lithium hydroxide monohydrate at 120℃; for 24h; Green chemistry;
75%	With C₁₅H₂₀MnN₂O₃S⁽¹⁺⁾*Br^(1-); potassium-t-butoxide In neat (no solvent) at 140℃; for 36h; Inert atmosphere; Green chemistry;
68%	With potassium-t-butoxide; C₂₂H₁₄N₂O In toluene at 70℃; for 8h; Irradiation; Green chemistry;
57%	With potassium-t-butoxide; Br^(1-)*C₁₆H₂₀MnN₂O₃S⁽¹⁺⁾; potassium hydroxide In tetrahydrofuran; toluene at 120℃; for 48h; Schlenk technique; Inert atmosphere; Sealed tube;

Reference： [1]Wei, Duo; Dorcet, Vincent; Darcel, Christophe; Sortais, Jean-Baptiste [ChemSusChem, 2019, vol. 12, # 13, p. 3078 - 3082]
[2]Bhattacharyya, Dipanjan; Adhikari, Priyanka; Deori, Kritartha; Das, Animesh [Catalysis science and technology, 2022, vol. 12, # 18, p. 5695 - 5702]
[3]Shee, Sujan; Ganguli, Kasturi; Jana, Kalipada; Kundu, Sabuj [Chemical Communications, 2018, vol. 54, # 50, p. 6883 - 6886]
[4]Hu, Wenkang; Zhang, Yilin; Zhu, Haiyan; Ye, Dongdong; Wang, Dawei [Green Chemistry, 2019, vol. 21, # 19, p. 5345 - 5351]
[5]Chai, Huining; Tan, Weiqiang; Lu, Yuanyuan; Zhang, Guangyao; Ma, Jiping [Applied Organometallic Chemistry, 2020, vol. 34, # 8]
[6]Parua, Seuli; Sikari, Rina; Sinha, Suman; Das, Siuli; Chakraborty, Gargi; Paul, Nanda D. [Organic and Biomolecular Chemistry, 2018, vol. 16, # 2, p. 274 - 284]
[7]Bains, Amreen K.; Singh, Vikramjeet; Adhikari, Debashis [Journal of Organic Chemistry, 2020, vol. 85, # 23, p. 14971 - 14979]
[8]Xu, Jing-Xiu; Pan, Nan-Lian; Chen, Jia-Xi; Zhao, Jin-Wu [Journal of Organic Chemistry, 2021, vol. 86, # 15, p. 10747 - 10754]
[9]Maji, Milan; Chakrabarti, Kaushik; Panja, Dibyajyoti; Kundu, Sabuj [Journal of Catalysis, 2019, vol. 373, p. 93 - 102]
[10]Das, Kalicharan; Mondal, Avijit; Srimani, Dipankar [Chemical Communications, 2018, vol. 54, # 75, p. 10582 - 10585]
[11]K. Bains, Amreen; Ankit, Yadav; Adhikari, Debashis [ChemSusChem, 2021, vol. 14, # 1, p. 324 - 329]
[12]Han, Mingyang; Lin, Qing; Liu, Qingbin; Liu, Song; Ma, Ning; Solan, Gregory A.; Sun, Wen-Hua; Wang, Zheng; Yan, Xiuli [Catalysis science and technology, 2021, vol. 11, # 24, p. 8026 - 8036]

30
[ 18728-61-5 ]
[ 37585-25-4 ]
[ 2227262-56-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With cesiumhydroxide monohydrate; C₁₇H₁₄Br₂CoN₄ In toluene at 150℃; for 6h; Sealed tube; Inert atmosphere;

Reference： [1]Shee, Sujan; Ganguli, Kasturi; Jana, Kalipada; Kundu, Sabuj [Chemical Communications, 2018, vol. 54, # 50, p. 6883 - 6886]

31
1-(pyridine-2-yl)ethanol [ No CAS ]
[ 13209-38-6 ]
[ 20364-46-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With C₁₅H₉BrMnN₃O₃; potassium <i>tert</i>-butylate In toluene at 110℃; for 12h; Inert atmosphere; Green chemistry;
66%	With C₁₅H₂₀MnN₂O₃S⁽¹⁺⁾*Br^(1-); potassium <i>tert</i>-butylate In neat (no solvent) at 140℃; for 36h; Inert atmosphere; Green chemistry;

Reference： [1]Chai, Huining; Tan, Weiqiang; Lu, Yuanyuan; Zhang, Guangyao; Ma, Jiping [Applied Organometallic Chemistry, 2020, vol. 34, # 8]
[2]Das, Kalicharan; Mondal, Avijit; Srimani, Dipankar [Chemical Communications, 2018, vol. 54, # 75, p. 10582 - 10585]

32
[ 18728-61-5 ]
[ 540-88-5 ]
[ 2555-01-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium t-butanolate In toluene at 100℃; for 1h; Sealed tube;

Reference： [1]Zhang, Chunyan; Zhang, Guoying; Luo, Shizhong; Wang, Chunfu; Li, Huiping [Organic and biomolecular chemistry, 2018, vol. 16, # 44, p. 8467 - 8471]

33
[ 2135825-21-5 ]
[ 18728-61-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With lithium hydroxide monohydrate	13 The ketone compound (1 mmol), pinacol borane (1.1 mmol), toluene (2 mL), and compound 2 (1 mol%) were put into a pressure-resistant bottle (10 mL), sealed under an argon atmosphere, and heated in an oil bath at 50°C Stir for 12 hours to obtain the organic boronate compound (99% yield by NMR detection). The reaction was stopped, the toluene solvent was removed, and the organic boronic ester was hydrolyzed to obtain a secondary alcohol product, and the yield was 94%.
94%	With lithium hydroxide monohydrate	13 The ketone compound (1 mmol), pinacol borane (1.1 mmol), toluene (2 mL), and compound 2 (1 mol%) were put into a pressure-resistant bottle (10 mL), sealed under an argon atmosphere, and heated in an oil bath at 50°C Stir for 12 hours to obtain the organic boronate compound (99% yield by NMR detection). The reaction was stopped, the toluene solvent was removed, and the organic boronic ester was hydrolyzed to obtain a secondary alcohol product, and the yield was 94%.
81%	With mesoporous silica In ethyl acetate; Petroleum ether

	With methanol; mesoporous silica at 60℃; for 6h;
	With mesoporous silica In methanol at 60℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox;
85.3 mg	With dihydrogen peroxide; sodium hydroxide Inert atmosphere;
116 mg	With lithium hydroxide monohydrate; mesoporous silica In ethyl acetate; Petroleum ether

Reference： [1]Current Patent Assignee: JIAXING UNIVERSITY - CN113943327, 2022, A Location in patent: Paragraph 0075-0077
[2]Current Patent Assignee: JIAXING UNIVERSITY - CN113943327, 2022, A Location in patent: Paragraph 0075-0077
[3]Qi, Xinghao; Zheng, Tingting; Zhou, Junhao; Dong, Yanhong; Zuo, Xia; Li, Xiaoyan; Sun, Hongjian; Fuhr, Olaf; Fenske, Dieter [Organometallics, 2019, vol. 38, # 2, p. 268 - 277]
[4]Sarkar, Nabin; Mahato, Mamata; Nembenna, Sharanappa [European Journal of Inorganic Chemistry, 2020, vol. 2020, # 23, p. 2295 - 2301]
[5]Sahoo, Rajata Kumar; Mahato, Mamata; Jana, Achintya; Nembenna, Sharanappa [Journal of Organic Chemistry, 2020, vol. 85, # 17, p. 11200 - 11210]
[6]Bodensteiner, Michael; Coburger, Peter; Demeshko, Serhiy; Gawron, Martin; Maier, Thomas M.; Meyer, Franc; Wolf, Robert; de Bruin, Bas; van Leest, Nicolaas P. [Inorganic Chemistry, 2020, vol. 59, # 21, p. 16035 - 16052]
[7]Luo, Jiabin; Cui, Chuanguo; Xiao, Zhiyin; Zhong, Wei; Lu, Chunxin; Jiang, Xiujuan; Li, Xueming; Liu, Xiaoming [Dalton Transactions, 2022, vol. 51, # 30, p. 11558 - 11566]

34
[ 18728-61-5 ]
[ 612-25-9 ]
[ 7491-86-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With C₂₂H₂₄ClIrN₃O⁽¹⁺⁾*Cl^(1-); potassium hydroxide In water at 120℃; for 24h; Green chemistry;

Reference： [1]Maji, Milan; Chakrabarti, Kaushik; Panja, Dibyajyoti; Kundu, Sabuj [Journal of Catalysis, 2019, vol. 373, p. 93 - 102]

35
[ 20988-55-0 ]
[ 23612-57-9 ]
[ 92404-56-3 ]

Reference： [1]Journal of Catalysis,2019,vol. 373,p. 93 - 102
[2]Green Chemistry,2019,vol. 21,p. 5345 - 5351

36
[ 18728-61-5 ]
[ 2342610-35-7 ]
[ 2342605-97-2 ]

Yield	Reaction Conditions	Operation in experiment
39%	With potassium <i>tert</i>-butylate In tetrahydrofuran for 0.5h;	55 Example 55: Synthesis of 3-(3-((6-(l-(pyridin-2-yl)ethoxy)pyridin-3-yl)methyl)isoxazol-5- yl)pyridin-2 -amine To a neat mixture of 3-(3-((6-fluoropyridin-3-yl)methyl)isoxazol-5-yl)pyridin-2 -amine (Intermediate E, 60 mg, 0.22mmol) and l-(pyridin-2-yl)ethan-l-ol (l64mg, l.33mmol) was added potassium 2-methylpropane-2-olate (1M in THF, 2.22mL, 2.22mmol) and the mixture was stirred for 30min. The mixture was transferred to a silica gel samplet which was subsequently loaded on to a Biotage Snap column. The residue was purified by column chromatography (Si02, hexane/ethyl acetate). Combined fractions were concentrated under reduced pressure. Residue was dissolved in acetonitrile (5mL) and water (lOmL), frozen and lyophilized to yield 3-(3-((6-(l-(pyridin-2-yl)ethoxy)pyridin-3- yl)methyl)isoxazol-5-yl)pyridin-2 -amine (32mg, 0.086mmol, 39%) as a white solid. MS: 374.1 [M+H]+.
39%	With potassium <i>tert</i>-butylate In tetrahydrofuran for 0.5h;	55 Synthesis of 3-(3-((6-(1-(pyridin-2-yl)ethoxy)pyridin-3-yl)methyl)isoxazol-5-yl)pyridin-2-amine To a neat mixture of 3-(3-((6-fluoropyridin-3-yl)methyl)isoxazol-5-yl)pyridin-2-amine (Intermediate E, 60 mg, 0.22mmol) and 1-(pyridin-2-yl)ethan-1-ol (164mg, 1.33mmol) was added potassium 2-methylpropane-2-olate (1M in THF, 2.22mL, 2.22mmol) and the mixture was stirred for 30min. The mixture was transferred to a silica gel samplet which was subsequently loaded on to a Biotage Snap column. The residue was purified by column chromatography (SiO2, hexane/ethyl acetate). Combined fractions were concentrated under reduced pressure. Residue was dissolved in acetonitrile (5mL) and water (10mL), frozen and lyophilized to yield 3-(3-((6-(1-(pyridin-2-yl)ethoxy)pyridin-3-yl)methyl)isoxazol-5-yl)pyridin-2-amine (32mg, 0.086mmol, 39%) as a white solid. MS: 374.1 [M+H]+.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2019/113542, 2019, A1 Location in patent: Paragraph 0445; 0446
[2]Current Patent Assignee: PFIZER INC - WO2020/247804, 2020, A1 Location in patent: Paragraph 0454-0455

37
[ 18728-61-5 ]
[ 2040-01-9 ]
[ 2363035-54-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium <i>tert</i>-butylate; C₁₄H₁₂BrMnN₂O₃S In toluene at 140℃; for 24h; Inert atmosphere; Sealed tube;
83%	With C₁₉H₂₁CoINO; potassium <i>tert</i>-butylate In toluene at 150℃; for 24h;

Reference： [1]Waiba, Satyadeep; Jana, Sayan K.; Jati, Ayan; Jana, Akash; Maji, Biplab [Chemical Communications, 2020, vol. 56, # 60, p. 8376 - 8379]
[2]Chakraborty, Priyanka; Gangwar, Manoj Kumar; Emayavaramban, Balakumar; Manoury, Eric; Poli, Rinaldo; Sundararaju, Basker [ChemSusChem, 2019, vol. 12, # 15, p. 3463 - 3467]

38
[ 18728-61-5 ]
[ 15128-82-2 ]
[ 2378319-77-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;	4.1.3. General procedure for the synthesis of 2-nitro-5-(1-(pyridin-2-yl)ethoxy)pyridine (5i) 1-(pyridin-2-yl)ethan-1-ol (20 mmol), PPh3 (30 mmol) and 2-nitro-3-hydroxyl pyridine (20 mmol) were dissolved in 30 mL THF under the N2 atmosphere. When the reaction was cooled to 0 °C, DEAD (30 mmol) was added dropwise. Then the reaction was warmed to room temperature for 3 h. The reaction mixture was evaporated and crystallized by EtOH-Pet. Yellow solid. Yield: 85%. 1H NMR (500 MHz, DMSO-d6) δ 8.62-8.55 (m, 1H), 8.08 (dd,J = 5.0, 1.5 Hz, 1H), 7.86-7.83 (m, 2H), 7.66 (dd, J = 8.5, 4.5 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.36-7.33 (m,1H), 5.82 (q, J = 6.5 Hz, 1H),1.62 (d, J = 6.5 Hz, 3H). HRMS (ESI) m/z calcd for C12H12N3O3 [M+H]+: 246.0873, Found: 246.0880.

Reference： [1]Chen, Wenteng; Guo, Xiao; Zhang, Can; Ke, Di; Zhang, Guolin; Yu, Yongping [European Journal of Medicinal Chemistry, 2019, vol. 183]

39
[ 18728-61-5 ]
[ 1667-01-2 ]
[ 2412097-39-1 ]

Yield	Reaction Conditions	Operation in experiment
48%	With trimethylamine-N-oxide; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one) irontricarbonyl complex3; sodium t-butanolate In toluene at 110℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;

Reference： [1]Bettoni, Léo; Gaillard, Sylvain; Renaud, Jean-Luc [Organic Letters, 2020]

40
1-(pyridine-2-yl)ethanol [ No CAS ]
[ 10517-50-7 ]
[ 20364-45-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	With C₁₅H₉BrMnN₃O₃; potassium <i>tert</i>-butylate In toluene at 110℃; for 12h; Inert atmosphere; Green chemistry;

Reference： [1]Chai, Huining; Tan, Weiqiang; Lu, Yuanyuan; Zhang, Guangyao; Ma, Jiping [Applied Organometallic Chemistry, 2020, vol. 34, # 8]

41
[ 18728-61-5 ]
[ 2454052-90-3 ]
[ 2454048-41-8 ]

Yield	Reaction Conditions	Operation in experiment
18%	Stage #1: 3-bromo-5-(8-chloroquinolin-6-yl)-6-(4-fluorophenyl)pyrazin-2-amine With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 1-(pyridine-2-yl)ethanol In N,N-dimethyl-formamide at 120℃; for 16h; Inert atmosphere;	S-16 Example S-16: Synthesis of 5-(8-chloroquinolin-6-yl)-6-(4-fluorophenyl)-3-(1-(pyridin-2-yl)ethoxy)pyrazin-2-amine (Compound No. 103) To a stirred solution of 3-bromo-5-(8-chloroquinolin-6-yl)-6-(4-fluorophenyl)pyrazin-2-amine (0.1 g, 0.23 mmol, 1.0 eq) in DMF (5 ml) was added Cs2CO3 (224 mg, 0.69 mmol, 3 eq) and it was stirred at RT for 5 min followed by the addition of 1-(pyridin-2-yl)ethanol (72 mg, 0.69 mmol, 2.5 eq) at RT under inert condition. The resulting mixture was stirred for 16 h at 120° C. Following this, ice cold water (20 mL) was added and extracted with ethyl acetate (320 mL), the combined organic layer washed with brine solution (150 mL), dried over Na2SO4, filtered and distilled purified by reverse phase column chromatography to get the title compound (20 mg, 18%). LCMS: 472 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 8.93 (d, 1H), 8.58 (d, 1H), 8.19 (d, 1H), 7.84 (t, 1H), 7.64 (d, 1H), 7.52-7.61 (m, 3H), 7.26-7.37 (m, 3H), 7.11 (t, 2H), 6.83 (br s, 2H), 6.20-6.25 (m, 1H), 1.70 (d, J=6.6 Hz, 3H).

Reference： [1]Current Patent Assignee: NUVATION BIO INC - US2020/231570, 2020, A1 Location in patent: Paragraph 0432-0433

42
[ 18728-61-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,10-Phenanthroline; oxygen; copper diacetate; silver nitrate; sodium hydroxide In dimethyl sulfoxide at 140℃; for 12h; Autoclave; Green chemistry;

Reference： [1]Chen, Bingfeng; Han, Buxing; Liu, Mingyang; Meng, Qinglei; Song, Jinliang; Zhang, Pei; Zhang, Zhanrong [Chemical Science, 2020, vol. 11, # 29, p. 7634 - 7640]

43
[ 18728-61-5 ]
[ 882-33-7 ]
[ 3111-54-4 ]

Yield	Reaction Conditions	Operation in experiment
80 %Chromat.	With 1,10-Phenanthroline; oxygen; potassium carbonate; copper(II) sulfate In dimethyl sulfoxide at 140℃; for 24h; Molecular sieve; Autoclave; Green chemistry;

Reference： [1]Chen, Bingfeng; Han, Buxing; Liu, Mingyang; Meng, Qinglei; Song, Jinliang; Zhang, Pei; Zhang, Zhanrong [Chemical Science, 2020, vol. 11, # 29, p. 7634 - 7640]

44
[ 18728-61-5 ]
[ 59-48-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
43%	With carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; potassium hydroxide In toluene at 150℃; for 16h; Inert atmosphere;
38%	With potassium <i>tert</i>-butylate; C₁₂H₁₉Cl₂MnN₃O In toluene at 110℃; for 14h; Sealed tube; Inert atmosphere; Schlenk technique;

Reference： [1]Chakraborty, Priyanka; Garg, Nidhi; Manoury, Eric; Poli, Rinaldo; Sundararaju, Basker [ACS Catalysis, 2020, vol. 10, # 14, p. 8023 - 8031]
[2]Rana, Jagannath; Nagarasu, Palaniyappan; Subaramanian, Murugan; Mondal, Akash; Madhu, Vedichi; Balaraman, Ekambaram [Organometallics, 2021, vol. 40, # 6, p. 627 - 634]

45
[ 18728-61-5 ]
[ 2460487-39-0 ]
[ 2460487-73-2 ]

Yield	Reaction Conditions	Operation in experiment
27%	With di-isopropyl azodicarboxylate; triphenylphosphine at 0℃; for 1h;	46.A Step A.6-chloro-N-(2,4-dimethoxybenzyl)-2-(1-(pyridin-2-yl)ethyl)-2H-[1,2,3]triazolo[4,5- c]pyridin-4-amine The mixture of 6-chloro-N-(2,4-dimethoxybenzyl)-3H-[1,2,3]triazolo[4,5-c]pyridin- 4-amine (1000 mg, 3.13 mmol), 1-(pyridin-2-yl)ethan-1-ol (462 mg, 3.75 mmol), triphenylphosphine (1641 mg, 6.25 mmol) and diisopropyl azodicarboxylate (0.739 mL, 3.75 mmol) was stirred at 0 °C for 1h. Direct purification on silica gel column afforded the desired product (359 mg, 27%). LC-MS calculated for C21H22ClN6O2: 425.1 (M+H)+; found: 425.3 (M+H)+.

Reference： [1]Current Patent Assignee: INCYTE CORP - WO2020/159905, 2020, A1 Location in patent: Page/Page column 42; 105

46
1-(pyridine-2-yl)ethanol [ No CAS ]
[ 67-56-1 ]
[ 2459-07-6 ]

Yield	Reaction Conditions	Operation in experiment
86 %Chromat.	With oxygen; potassium carbonate at 150℃; for 24h; Autoclave;
66 %Chromat.	With oxygen; potassium carbonate at 130℃; for 12h; Autoclave;	23 Example 23 Add Co-NC (5mol%), 2-(1-hydroxyethyl)pyridine (1mmol), K2CO3 (20mol%), and 4mL methanol to a 25mL polytetrafluoroethylene-lined autoclave. Seal the reactor. Fill the reactor with oxygen pressure to 0.4MPa, put the reactor in an oil bath at 130°C, and stir for 12h at 400 speed. After the reaction, the reactor is cooled to room temperature, the reactor is opened, and the internal standard biphenyl (60mg) is added in the gas phase. The qualitative products were detected by chromatography-mass spectrometry, and the yields of the substrate 2-(1-hydroxyethyl)pyridine and the product methyl 2-picolinate were quantified by gas chromatography internal standard method in Table 1.

Reference： [1]Dai, Wen; Gao, Shuang; Li, Guosong; Luo, Huihui; Lv, Ying; Shang, Sensen; Wang, Lianyue [Angewandte Chemie - International Edition, 2020, vol. 59, # 43, p. 19268 - 19274][Angew. Chem., 2020, vol. 132, # 43, p. 19430 - 19436,7]
[2]Current Patent Assignee: Dalian Institute of Chemical Physics (in: CAS); CHINESE ACADEMY OF SCIENCES - CN112876355, 2021, A Location in patent: Paragraph 0076-0077; 0092

47
[ 18728-61-5 ]
[ 50-01-1 ]
[ CAS Unavailable ]
[ 2700029-82-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium hydroxide In 1,4-dioxane at 120℃; for 36h;

Reference： [1]Borthakur, Ishani; Guria, Saikat; Kundu, Sabuj; Maji, Milan; Singha, Suman [Journal of Catalysis, 2021, vol. 402, p. 37 - 51]

48
[ 18728-61-5 ]
[ 457606-56-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium-t-butoxide; hydrazine hydrate monohydrate In toluene at 80℃; for 12h;	2.5 General procedure for synthesis of azines using alcohols General procedure: A mixture of catalyst 1 (1mol %), KOtBu (5mol %), primary alcohol (0.5mmol), and hydrazine hydrate (1mmol) was loaded in a round bottomed flask containing 3mL of toluene and stirred at 80°C for 12h. The mixture was then cooled to room temperature and extracted using distilled water (5mL) and dichloromethane (5mL). The organic layer was passed through sodium sulphate to remove the moisture. The residue was purified using silica gel column chromatography with eluent petroleum ether (60-80°C) and ethyl acetate (9:1, v/v) to obtain the desired product.

Reference： [1]Gayathri; Viswanathamurthi; Naveen; Murugan [Inorganica Chimica Acta, 2022, vol. 537]

49
[ 18728-61-5 ]
[ 113-00-8 ]
[ CAS Unavailable ]
[ 1071698-47-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium-t-butoxide; Zn(2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline)Cl<SUB>2</SUB>; zinc powder In toluene at 100℃; for 16h;

Reference： [1]Das, Siuli; Guin, Amit Kumar; Mondal, Rakesh; Paul, Nanda D. [Organic and Biomolecular Chemistry, 2022, vol. 20, # 15, p. 3105 - 3117]

50
[ 18728-61-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
86 %Chromat.	With ammonia; oxygen In 1,4-dioxane at 150℃; for 12h; Autoclave;	General procedure for oxidative cleavage and amidation reactions General procedure: In a typical procedure, MnOx (40 mg), alcohol (0.25 mmol), and dioxane (2 mL)were added into a glass tube (10 mL volume) with a magnetic stir bar. After beingfitted with a polytetrafluoroethylene (PTFE) stopper with a pinhole, the tube wasplaced into an autoclave. Subsequently, the autoclave was flushed with oxygenthree times and then charged with O2 (0.5 MPa) and NH3 (0.5 MPa). Finally, theautoclave was placed into an oil bath and stirred at 150°C (bath temperature)for the required time. After the completion of the reaction, the autoclave wascooled to room temperature, and the tube was removed from the autoclave.Naphthalene (20 mg) as the internal standard was added into the tube, and thecrude mixture was diluted with dioxane (2 mL), followed by filtration and analysisby GC and GC-MS.

Reference： [1]He, Peipei; Chen, Bo; Huang, Liang; Liu, Xixi; Qin, Jingzhong; Zhang, Zehui; Dai, Wen [Chem, 2022, vol. 8, # 7, p. 1906 - 1927]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	18728-61-5	MDL No. :	MFCD06245419
Formula :	C₇H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	123.15	Pubchem ID :	-
Synonyms :

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.17
TPSA :	33.12 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.89 cm/s

Log Po/w (iLOGP) :	1.54
Log Po/w (XLOGP3) :	0.23
Log Po/w (WLOGP) :	0.81
Log Po/w (MLOGP) :	0.22
Log Po/w (SILICOS-IT) :	1.35
Consensus Log Po/w :	0.83

[ CAS No. 18728-61-5 ] {[proInfo.proName]}

Quality Control of [ 18728-61-5 ]

Related Doc. of [ 18728-61-5 ]

Product Details of [ 18728-61-5 ]

Calculated chemistry of [ 18728-61-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 18728-61-5 ]

Application In Synthesis of [ 18728-61-5 ]

[ 18728-61-5 ] Synthesis Path-Downstream 1~50

Related Functional Groups of
[ 18728-61-5 ]

Alcohols

Related Parent Nucleus of
[ 18728-61-5 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.18
Solubility :	8.22 mg/ml ; 0.0667 mol/l
Class :	Very soluble
Log S (Ali) :	-0.49
Solubility :	40.3 mg/ml ; 0.327 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.84
Solubility :	1.78 mg/ml ; 0.0145 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.7

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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Prevention
Code	Phrase
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P222	Do not allow contact with air.
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P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P320
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P321
P322
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P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
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P413
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P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling