2-Fluorobenzoyl chloride → N-benzyl-2-(2-chloro-5-fluorobenzamido)-isonicotinamide

Participants

Reaction Steps

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 2-chloro-5-fluorobenzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(2-chloro-5-fluorobenzamido)-isonicotinamide was obtained as a colorless solid in 57% yield: mp 180-181° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) (9.15 (d, J=13.8 Hz, 1H), 8.60 (s, 1H), 8.44 (d, J=5.0 Hz, 1H), 8.07 (dd, J=6.6, 2.8 Hz, 1H), 7.58 (d, J=4.2 Hz, 1H), 7.52-7.46 (m, 1H), 7.36-7.12 (m, 6H), 6.67 (s, 1H), 4.65 (d, J=5.7 Hz, 2H); MS (ES+) m/z 384.5 (M+1).

Provenance & Evidence