N-Iodosuccinimide → 4-Iodofuro[2,3-c]pyridin-7-amine

Participants

Reaction Steps

To a solution of furo[2,3-c]pyridine-7-ylamine (1.5 g, 11.2 mmol) in acetonitrile (40 mL) was added NIS (3.02 g, 13.4 mmol) portionwise over a period of 15 min. The resultant mixture was stirred at RT for 16 h. The reaction mixture was quenched with 20% aqueous sodium thiosulfate solution (20 mL) and stirred for 10 min. The mixture was extracted with ethyl acetate (70 mL). The organic layer was washed with aqueous 20% sodium thiosulfate solution (20 mL), water (2×50 mL), and brine (40 mL), dried over sodium sulfate, filtered, and concentrated. Purification of the residue by column chromatography (25% ethyl acetate:hexanes) afforded 2.5 g (86%) of the title compound.

Provenance & Evidence