Acetic Acid → 4-Bromo-3-((dimethylamino)methyl)-1H-indole-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

Acetic acid (1.15 mL, 20.08 mmol) was added to a suspension of 4-bromo-1H-indole-7-carboxamide (3 g, 12.55 mmol), paraformaldehyde (0.603 g, 20.08 mmol) and dimethylamine (2 M in methanol, 10 mL, 20.08 mmol) in ethanol (50 mL). The mixture was heated to 80° C. After 2 h, the ethanol was removed under vacuum. The residue was partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine (15 mL), dried and concentrated to afford the crude desired product as a light brown solid (4.08 g). LCMS (M+H)+ m/z 295.8, 297.8.

Provenance & Evidence