Dimethylamine → 5-bromo-2-methoxy-N,N-dimethylnicotinamide

Participants

Reaction Steps

To a mixture of 5-bromo-2-methoxynicotinic acid (80 mg, 0.34 mmol), triethylamine (192 μl, 1.38 mmol) and 2-(1 H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate in acetonitrile (1 mL) was added dimethylamine, 2 M in tetrahydrofuran (172 μl, 0.34 mmol). The reaction mixture was stirred at ambient temperature under an atmosphere of nitrogen for 3 h. The mixture was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated in vacuo to give a crude product which was purified by column chromatography using a gradient of ethyl acetate in heptane affording 54 mg (60%) of the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) ppm 8.36 (d, 1 H), 7.91 (d, 1 H), 3.88 (s, 3 H), 2.96 (s, 3 H), 2.78 (s, 3 H); MS (ESI) m/z 259, 261[M+H+].

Provenance & Evidence