Benzenesulfonyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-1H-pyrrolo[2,3-b]pyridine (2 g, 10.15 mmol) in DMF (50 mL) stirred at 0° C. was added sodium hydride (0.487 g, 12.18 mmol). After stirring for 30 min at 0° C., benzenesulfonyl chloride (1.570 mL, 12.18 mmol) was added to the mixture and stirred at 0° C. for 1.5 hour. The reaction was quenched with addition of saturated NH4Cl aq. solution and the mixture was poured into saturated aq. NH4Cl (100 mL). The mixture was extracted with ethyl acetate (20 mL×3). The organic layers were combined, washed with brine (100 mL), dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with a gradient of 0-25% ethyl acetate in cyclohexane to give the title compound (3.39 g). LCMS (A): m/z (M+H)+ 337/339, C13H9BrN2O2S requires 336/338 (acidic).

Provenance & Evidence