Methanol → 2-bromo-N-(4-fluorobenzyl)-5-hydroxyisonicotinamide

Participants

Reaction Steps

BBr3 (20 mL) was added dropwise to a mixture of 2-bromo-N-(4-fluorobenzyl)-5-methoxyisonicotinamide (2.0 g, 5.9 mmol) in DCM (10 mL) at −78° C. The mixture was stirred at RT for 10 h, and then MeOH (20 mL) was added to quench the reaction. The mixture was concentrated in vacuum to give the product of compound 2-bromo-N-(4-fluorobenzyl)-5-hydroxyisonicotinamide (1.8 g, yield: 95%). 1H-NMR (DMSO-d6, 400 MHz) δ 11.9 (s, 1H), 9.35 (s, 1H), 8.16 (s, 1H), 7.90 (s, 1H), 7.38 (t, J=6.0 Hz, 2H), 7.16 (d, J=8.8 Hz, 2H), 4.78 (s, 2H). MS (M+H)+: 325/327.

Provenance & Evidence