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

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(1-benzenesulfonyl-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanol (710 mg, 1.71 mmol) in dichloromethane (50 mL) was added Dess-Martin periodinane (1.8 g, 4.2 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 (60 mL). The mixture was extracted with ethyl acetate (250 mL), washed with a saturated aqueous sodium bicarbonate solution (3×50 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to give 1-(1-benzenesulfonyl-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanone (704 mg, quant.) as a light yellow solid which was used in the next step without further purification: LC/MS m/e calcd for C22H24N2O4S [M+H]+ 413.51, observed 413.2.

Provenance & Evidence