Dimethylamine → 6-Bromo-1-cyanomethyl-1H-indole-3-carboxylic Acid Dimethylamide

Participants

Reaction Steps

To a suspension of 6-bromo-1-cyanomethyl-1H-indole-3-carboxylic acid (0.478 g, 1.71 mmole) in dichloroethane (100 ml) was added oxalyl chloride (2.6 g, 20.55 mmole) at room temperature followed by a few drops of anhydrous DMF. The reaction was stirred at the same temperature for 24 h. To this mixture was added dimethyl amine (21.4 ml, 2 N in THF, 42.8 mmole) slowly. The reaction mixture was then poured into water (200 ml) and the organic phase was separated, evaporated to dryness and the residue was purified by column chromatography (silica gel, hexane:ethyl acetate 1:1). The pure product weighed 0.335 g (63% yield).

Provenance & Evidence