Dimethylformamide → 2-(4-bromo-pyridin-2-yl)-2-cyano-N,N-dimethyl-acetamide

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (186.2 mg, 4.65 mmol, 60% dispersion in oil) was added to a solution of 2-cyano-N,N-dimethyl-acetamide (373.7 mg, 3.33 mmol) in dimethylformamide (10 mL) at 0° C. The mixture was removed from the ice bath for 20 min, and a solution of 2,4-dibromopyridine (300 mg, 1.33 mmol) in dimethylformamide (3 mL) was quickly added. The mixture was heated at 60° C. for 16 h. The reaction was cooled to room temperature, quenched by addition of 200 μL saturated ammonium chloride and concentrated to a residue. The compound was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 2-(4-bromo-pyridin-2-yl)-2-cyano-N,N-dimethyl-acetamide and 2-(3-bromo-pyridin-4-yl)-2-cyano-N,N-dimethyl-acetamide.

Provenance & Evidence