Bromine → N-{4-[(3-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluorophenyl}acetamide

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Reaction Conditions

Reaction Steps

1.05 g (3.45 mmol) of N-[3,5-difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]acetamide are dissolved in 35 ml of glacial acetic acid and, using an ice bath, cooled to about 10° C. 4.8 ml (4.8 mmol) of a 1M solution of bromine in dichloromethane are added, and the mixture is stirred at 20° C. for about 30 min, resulting in the precipitation of a solid. The solid is filtered off with suction and washed with ethyl acetate. The mother liquor is neutralized using conc. aqueous sodium hydroxide solution and extracted with ethyl acetate. The crystals that were filtered off with suction are dissolved in 3 ml of DMF. The mixture is diluted with ethyl acetate and extracted three times with 1N sodium hydroxide solution. The combined organic phases are dried over magnesium sulfate. The solvent is removed under reduced pressure. The product is reacted without further purification.

Provenance & Evidence