N-bromobutanimide → 5-Bromo-2,3-dihydro-7-azaindole

Participants

Reaction Steps

The resulting 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (614 mg, 5.11 mmol) and N-bromosuccinimide (1.09 g, 6.13 mmol) were dissolved in N,N-dimethylformamide (12 mL), and the solution was stirred for 2.5 hours at room temperature. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=3:1), and 5-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (370 mg, 1.86 mmol, 36%) was obtained as a white solid.

Provenance & Evidence