反应详情

To a solution of 2-amino-N-benzylisonicotinamide (0.10 g, 0.44 mmol) and 4-dimethylaminopyridine (0.01 g, 0.08 mmol) in pyridine (3.0 mL) was added 2-fluorobenzoyl chloride (0.07 g, 0.44 mmol). The resulting solution was stirred at ambient temperature for 16 hours, diluted with dichloromethane (25 mL), washed with water (2×25 mL) and brine (10 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with 45% ethyl acetate in hexanes to give N-benzyl-2-(2-fluorobenzamido)isonicotinamide as a colorless solid (0.07 g, 44%): mp 175-176° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 9.21 (d, J=13.7 Hz, 1H), 8.64 (s, 1H), 8.46-8.42 (m, 1H), 8.12-8.06 (m, 1H), 7.64-7.48 (m, 2H), 7.35-7.16 (m, 7H), 6.68 (s, 1H), 4.65 (d, J=5.7 Hz, 2H); 13C NMR (CDCl3, 75 MHz) δ 165.2, 162.1, 161.9, 158.8, 151.7, 148.8, 144.1, 137.5, 134.5, 134.4, 131.9, 128.8, 127.7, 125.1, 120.7, 118.8, 116.6, 116.3, 111.0, 44.2; MS (ES+) m/z 350.6 (M+1).

1. washwashed with water (2×25 mL) and brine (10 mL)
2. dry with materialThe organic solution was dried over anhydrous sodium sulphate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe residue was purified by column chromatography
6. washeluting with 45% ethyl acetate in hexanes