Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-5-bromo-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

To a well stirred solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (10.0 g, 50.7 mmol) in dry THF (100 mL) was added NaH (60% oil suspension; 3.0 g, 75 mmol) at 0° C. and stirred for 30 min. Phenylsulfonyl chloride (10.7 g, 60 mmol) was added slowly and the mixture was stirred at ambient temperature for 16 h (TLC monitoring: 60% ethyl acetate in hexanes). Solvent was removed under reduced pressure, water (25 mL) was added to the residue, and the mixture was extracted with dichloromethane (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue thus obtained was crystallized from dichloromethane to yield the title compound (13.0 g, 76%). 1H NMR (CDCl3, 300 MHz): δ=6.55 (d, J=4.2 Hz, 1H), 7.46-7.62 (m, 3H), 7.74 (d, J=4.0 Hz, 1H), 7.97 (d, J=2.1 Hz, 1H), 8.15-8.18 (m, 2H), 8.44 (d, J=2.1 Hz, 1H).

Provenance & Evidence