N-Iodosuccinimide → HCID 59525912, compound

Participants

Reaction Steps

To a solution of 2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide (2.8 g, 12.0 mmol) in dimethylformamide (40 mL) and dichloromethane (80 mL) was added slowly N-iodosuccinimide (1.060 g, 4.71 mmol). After twenty minutes, the reaction mixture was diluted with ethyl acetate (400 mL), hexanes (40 mL), and saturated aqueous sodium bicarbonate (100 mL) and filtered through a Buchner funnel. The layers of the filtrate were separated, and the organic layer was washed with water (3×100 mL, filtering before separated layers as above) and a 5:1 mixture of brine:saturated aqueous sodium thiosulfate (120 mL). The resulting organic layer was dried over sodium sulfate, filtered through a pad of Celite, and concentrated. The resulting solid was triturated with a mixture of dichloromethane, ethyl acetate, methanol, and dichloromethane to afford the title compound as a purple powder.

Provenance & Evidence