HCID 67229219, compound → HCID 67227818, compound

Participants

Reaction Steps

To a stirred solution of 1-{4-[1-(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-ethanone (300 mg, 0.6 mmol) in dry tetrahydrofuran (5 mL) was added a methylmagnesium chloride solution in tetrahydrofuran (3 M, 2 mL, 6 mmol) at 0° C. The resulting mixture was stirred at room temperature for 2 h, quenched with an ammonium chloride solution, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 25% ethyl acetate/hexanes) afforded 2-{4-[1-(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-propan-2-ol (160 mg, 51.8%) as a light yellow solid: LC/MS m/e calcd for C30H32N2O4S [M+H]+ 517.66, observed 517.1.

Provenance & Evidence