Methanesulfonyl chloride → 2-(5-Cyanopyridin-2-yl)ethyl methanesulfonate
Reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[N:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C(Cl)Cl>[CH3:12][S:13]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]#[N:11])=[CH:8][N:9]=1)(=[O:15])=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
NaBH4 (2.5 g, 67 mmol) was added in small portions to a solution of 6-(2-oxoethyl)pyridine-3-carbonitrile (5.0 g, crude) in 80 mL of MeOH at 0° C. The mixture was stirred at room temperature for 30 minutes and poured to 50 mL of water. The mixture was extracted with EtOAc (100 mL×5) and the combined organic layer was condensed. The residue was purified by flash chromatography to afford 6-(2-hydroxyethyl)pyridine-3-carbonitrile. TEA (2.1 g, 21 mmol) was added drop wise to a solution of 6-(2-hydroxyethyl)pyridine-3-carbonitrile (3.0 g, 20 mmol) and MsCl (2.3 g, 20 mmol) in 200 mL of DCM at 0° C. The mixture was stirred at RT for 30 minutes and washed with water and brine, dried over anhydrous Na2SO4 and condensed under vacuum below 30° C. to afford the title compound which was used immediately without further purification.