Triethylamine → 5-Bromo-N-(4-fluorobenzyl)-2-methoxynicotinamide

Participants

Reaction Steps

T3P (8.2 g, 25.8 mmol) was added to a solution of 5-bromo-2-methoxynicotinic acid (3 g, 12.9 mmol), (4-fluorophenyl)methanamine (1.6 g, 12.9 mmol) and Et3N (3.9 g, 38.7 mmol) in DCM (50 mL) at 0° C. The mixture was stirred at RT for 1 h. Water (50 mL) was added and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4. After being concentrated, the residue was purified by column chromatography (PE:EtOAc=4:1) to give the product of 5-bromo-N-(4-fluorobenzyl)-2-methoxynicotinamide (4.0 g, yield: 91%). 1H-NMR (CDCl3, 400 MHz) δ 8.64 (d, J=2.4 Hz, 1H), 8.31 (d, J=2.4 Hz, 1H), 8.17 (s, 1H), 7.32 (dd, J=5.2, 8.4 Hz, 2H), 7.04 (t, J=8.8 Hz, 2H), 4.63 (d, J=6.0 Hz, 2H), 4.05 (s, 3H). MS (M+H)+: 339/341

Provenance & Evidence