Benzenesulfonyl chloride → 1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

To a mixture of 5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine (2.7 g, 15.2 mmol), sodium hydroxide (1.82 g, 45.6 mmol) and tetrabutylammonium bromide (150 mg, 0.46 mmol) in dichloromethane (30 mL) at 0° C. was added benzenesulfonyl chloride (4.0 g, 22.8 mmol) dropwise. After stirring for 12 h at room temperature, the mixture was washed with water (2×10 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 50% dichloromethane/hexanes) to afford 1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine (2.68 g, 63%): LC/MS m/e calcd for C15H14N2O2S2 [M+H]+ 319.42, observed 319.1.

Provenance & Evidence