Benzenesulfonyl chloride → 6-Methoxy-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

To a mixture of 6-methoxy-1H-pyrrolo[2,3-b]pyridine (1.2 g, 8.1 mmol), sodium hydroxide (0.97 g, 24.3 mmol) and tetrabutylammonium bromide (78.4 mg, 0.24 mmol) in dichloromethane (50 mL) at 0° C. was added benzenesulfonyl chloride (2.14 g, 12.15 mmol) dropwise. The resulting mixture was stirred for 12 h at room temperature. The mixture was washed with water (2×10 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue which was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 100% dichloromethane) to afford 1-benzenesulfonyl-6-methoxy-1H-pyrrolo[2,3-b]pyridine (2.0 g, 85%): LC/MS m/e calcd for C14H12N2O3S [M+H]+ 290.33, observed 289.0.

Provenance & Evidence