Ammonium Chloride → 2-Chloro-5-fluoropyridine-3-carboxamide

Participants

Reaction Steps

A suspension of 2-chloro-5-fluoro-nicotinic acid (2.0 g, 11.39 mmol), HOBt (2.31 g, 17.13 mmol), BOP—Cl (4.37 g, 17.15 mmol), ammonium chloride (1.22 g, 22.86 mmol), DIPEA (12 ml, 66.74 mmol) in DMF (75 ml) was stirred at ambient temperature for 18 hours. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic phases were dried over MgSO4, filtrated and evaporated. The crude product was purified by column chromatography (silica gel, EtOAc) to obtain 2-chloro-5-fluoro-nicotinamide (850 mg, 4.9 mmol; 43%) as white solid. MS (m/e): 175.1 [M+H+].

Provenance & Evidence