Triacetoxyperiodinane → 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanone

Participants

Reaction Conditions

Reaction Steps

To a 250 mL round bottomed flask charged with 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol (12.5 g, 32.2 mmol) in dichloromethane (300 mL) was added Dess-Martin periodinane (17.8 g, 41.9 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 1 h and then quenched with a saturated aqueous sodium bicarbonate solution (200 mL). The mixture was extracted with ethyl acetate (500 mL), washed with a saturated aqueous sodium bicarbonate solution (3×150 mL), brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanone (9.9 g, 80%) as a light yellow solid which was used in the next step without further purification: LC/MS m/e calcd for C20H19FN2O3S [M+H]+ 387.45, observed 387.1.

Provenance & Evidence