Hydrogen Peroxide → N-[3-Fluoro-4-({3-(2-hydroxyethyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide

Participants

Reaction Steps

At 0° C., 890 mg (1.91 mmol) of N-[3-fluoro-4-({1-[(4-methylphenyl)sulfonyl]-3-vinyl-1H-pyrrolo[2,3-b]-pyridin-4-yl}oxy)phenyl]acetamide are initially charged in 28 ml of THF. 7.65 ml (7.65 mmol) of a 1M solution of borane in THF are added dropwise, and the mixture is stirred at RT for one hour. 14 ml of 1N aqueous sodium hydroxide solution and 14 ml of 30% strength hydrogen peroxide solution are then added carefully to the reaction mixture. The mixture is heated at 60° C. for one hour. For work-up, the reaction solution is partitioned between ethyl acetate and sodium bicarbonate solution. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried over sodium sulfate. The solvent is removed under reduced pressure. The product is purified by chromatography-on silica gel (mobile phase: dichloromethane/acetone 20:1 to 6.5:1).

Provenance & Evidence