General procedure for the synthesis of 2-fluoronicotinamide from 2-fluoronicotinic acid: thionyl chloride (40 mL) was added to 2-fluoronicotinic acid (2.0 g, 14.3 mmol) and the reaction mixture was refluxed for 18 hours. Upon completion of the reaction, it was cooled to room temperature and concentrated under reduced pressure. Benzene (100 mL) was added to the residue, followed by passing ammonia into the suspension for 3 hours. The reaction flask was sealed and stirring was continued for 18 hours, after which it was concentrated under reduced pressure. Water was added to the residue and extracted with ethyl acetate (EtOAc). The organic phase was washed sequentially with water and brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give 2-fluoronicotinamide (0.6 g, 30% yield). Mass spectrum (electrospray ionization, ES) showed m/z 141.1 ([M + H]+). 1H NMR (400 MHz, CDCl3) δ 8.32 (d, 1H, J = 4.5 Hz), 8.17 (m, 1H), 7.92 (br s, 1H), 7.79 (br s, 1H), 7.44 (m, 1H).
