2-(3-METHYLPYRIDIN-2-YL)ACETONITRILE synthesis

Yield:38203-11-1 100%

Reaction Conditions:

with n-butyllithium in tetrahydrofuran;hexanes at -78; for 2.08333 h;

Steps:

129.b

2-(3-Methylpyridine-2-yl)acetonitrile: To a solution of n-BuLi (2.5 N in hexanes, 7.92 mL, 19.8 mmol) at -78° C. under N₂ was added dry THF (75 mL), followed immediately by a solution of dry MeCN (1.15 mL, 21.78 mmol) in anhydrous THF (30 mL) over a 5-min period. The resulting reaction mixture was stirred continuously at -78° C. for 1 h. Then 2-bromo-3-methylpyridine (516 mg, 3 mmol) was added. The resulting reaction mixture was stirred at -78° C. for 1 h, then warmed to room temperature, and quenched with water. The organic solvent was evaporated in vacuo, dissolved in CH₂Cl₂. The organic layer was washed with brine, dried (MgSO₄), concentrated, purified via column chromatography (20% EtOAc in hexanes) to afford the product quantitatively: m/e=133 [M+1].

References:

US2005/84506,2005,A1 Location in patent:Page/Page column 79