Tetrahydrofuran → (3-amino-2,6-difluorophenyl)(5-iodo-1H-pyrrolo[2,3-b]pyridin-3-yl)methanone

Participants

Reaction Conditions

Reaction Steps

In a reaction vial, (2,6-difluoro-3-nitro-phenyl)-(5-iodo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (45, 0.123 g, 0.287 mmol) is mixed with 5.0 mL of ethyl acetate and 5.0 mL of tetrahydrofuran. Stannous chloride, dehydrate (0.223 g, 0.989 mmol) is added and the reaction is heated at 60° C. for 24 hours. The reaction is poured into a mixture of 25 mL of water and 25 mL of saturated aqueous sodium bicarbonate and treated with celite, then filtered through a bed of celite. The celite is washed with ethyl acetate. The organic layer is separated and washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (46, 0.100 g). MS (ESI) [M+H+]+=399.9.

Provenance & Evidence