Hydrochloric Acid → HCID 57731538, compound

Participants

Reaction Steps

To a mixture of 5-bromo-3-(1H-indol-7-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (802 mg, 1.7 mmol) and 2-tert-butoxycarbonylamino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (641 mg, 1.7 mmol) in a 20 mL microwave reaction flask was added THF (6 mL), acetonitrile (6 mL) and sodium carbonate (6 mL, 1 N aqueous solution, 6 mmol). The mixture was purged with nitrogen for 1 minute. Dichloro[1,1′-bis(diphenylphoshino)ferrocene]palladium(II) dichloromethane adduct (122 mg, 170 μmol) was added and the purging continued for another minute. The flask was sealed and irradiated in a microwave reactor to 70° C. for 15 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 2-tert-butoxycarbonylamino-5-[3-(1H-indol-7-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid methyl ester as a yellow solid (605 mg, 56% yield). MS: m/z 637 (M+H+).

Provenance & Evidence