Hydrochloric Acid → HCID 57731579, compound

Participants

Reaction Steps

To a mixture of 5-bromo-3-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1 g, 2.1 mmol) and 1H-indole-7-boronic acid (338 mg, 2.1 mmol) in a 20 mL microwave reaction flask was added THF (6.5 mL), acetonitrile (6.5 mL) and sodium carbonate (6.5 mL, 1 N aqueous solution, 6.5 mmol). The mixture was purged with nitrogen for 1 minute. Dichloro[1,1′-bis(diphenylphoshino)ferrocene]-palladium(II) dichloromethane adduct (164 mg, 0.2 mol) was added and the purging continued for another minute. The flask was sealed and irradiated in a microwave reactor to 60° C. for 30 minutes. Saturated sodium chloride (15 mL) was added and the pH was adjusted to 7 using hydrochloric acid (1 N). The resulting mixture was extracted with ethyl acetate (10 mL×3). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane to afford 5-bromo-3-(1H-indol-7-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine as a light brown solid (802 mg, 82% yield). MS: m/z 466 (M+H+).

Provenance & Evidence