Methyl 5-chloro-6-cyano-2-(3-fluorophenyl)nicotinate → Methyl 6-(aminomethyl)-5-chloro-2-(3-fluorophenyl)nicotinate

Participants

Reaction Steps

Methyl 5-chloro-6-cyano-2-(3-fluorophenyl)nicotinate (1.3 g, 4.5 mmol) was stirred in methanol (60 mL), and 5% palladium on carbon (1.0 g) was added. The mixture was degassed three times and placed under a balloon pressure of hydrogen for 4 hours. A solution of 0.5 M sodium methoxide in methanol (45 mL) was added and the mixture was filtered through celite. The filtrates were evaporated and the residue was triturated with dichloromethane. The solids were filtered and washed with dichloromethane to give the desired compound contaminated with 30% dechlorinated byproduct (1.3 g, 100%). LCMS calculated for C14H13ClFN2O2 (M+H)+: m/z=295.1. found: 295.0.

Provenance & Evidence