Acetyl chloride → HCID 59741014, compound

Participants

Reaction Conditions

Reaction Steps

5.00 g (17.9 mmol) of 3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline hydrochloride are suspended in 100 ml of dichloromethane and cooled to 0° C. 9.97 ml (71.5 mmol) of triethylamine and 3.81 ml (53.6 mmol) of acetyl chloride are added dropwise, and the mixture is stirred at 0° C. for another 2 hours. Saturated sodium bicarbonate solution is added, and the mixture is stirred at RT for 10 min. The mixture is then extracted twice with dichloromethane. Insoluble components are dissolved using a little acetone, and the mixture is diluted with dichloromethane and washed with saturated sodium chloride solution. The combined organic phases are dried over magnesium sulfate and the solvent is removed under reduced pressure. The crude product is taken up in 100 ml of ethanol. 3.31 ml (17.9 mmol) of 5.4 M sodium methoxide solution are added, and the mixture is stirred at RT for 30 min. The mixture is concentrated and the product is purified by chromatography on silica gel (mobile phase: dichloromethane/methanol (7N ammonia) 100:1 to 100:5).

Provenance & Evidence