N-bromobutanimide → 3-bromo-5-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

To a stirred solution of 5-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.832 g, 2.46 mmol) in tetrahydrofuran (12.3 ml) was added N-bromosuccinimide (0.875 g, 4.92 mmol). The reaction mixture was stirred at room temperature for 16 hours. The reaction was quenched with 10% aqueous sodium thiosulfate solution (50 mL), then extracted with EtOAc (2×50 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The crude residue was adsorbed on to silica gel and purified by silica gel chromatography (EtOAc/Hexanes gradient) to afford 3-bromo-5-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine as a white solid. LRMS (ESI) calculated for C17H13BrN4O2S [M+H]+, 417.0; found 417.0.

Provenance & Evidence