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

Participants

Reaction Steps

To a stirred suspension of sodium hydride (1.12 g; 60% dispersion in mineral oil) in THF (3 ml) kept below 15° C., a suspension of 4-bromo-1H-pyrrolo[2,3-b]pyridine (5 g) (prepared for example, according to the method described in Organic Letters, 2003, 5, 5023) in THF (27 ml) was added over 20 minutes. The reaction was left to stir for 10 minutes. Then a solution of benzenesulfonyl chloride (3.6 ml) in THF (6 ml) was added over 5 minutes. The reaction was left to stir at RT for 1 hour, then 0.5M hydrochloric acid solution (10 ml) was added. The layers were separated and the organic layer washed with brine, dried over magnesium sulphate and the solvent removed in vacuo and left on the vacuum line for 3 days. The solid was triturated using methanol (30 ml) then dried in the oven for 5 hours to give the title compound as a pale pink solid (7.42 g).

Provenance & Evidence