Methanol → HCID 44544213, compound

Participants

Reaction Steps

1,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-2-(5-methanesulfonyl-1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)-4-methylpentan-2-ol (179 mg, 0.37 mmol) was dissolved in 10 mL of dichloromethane. 3.7 mL of a 1 M solution of boron tribromide (3.7 mmol) in dichloromethane were added. The resulting solution was stirred at normal room temperature overnight. After dropwise addition of MeOH (1 mL) at 0° C., the solvent was evaporated. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate (NaHCO3) solution. The organic phase was separated and the aqueous layer was extracted with four 10 mL portions of ethyl acetate. The combined organic phases were dried over magnesium sulfate. The solvent was removed. Flash chromatography of the residue yielded 4-fluoro-2-[4,4,4-trifluoro-3-hydroxy-3-(5-methanesulfonyl-1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)-1,1-dimethylbutyl]phenol as a white solid.

Provenance & Evidence