1H-Pyrrolo(2,3-b)pyridine → 3-Bromo-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

To a solution of 1H-pyrrolo[2,3-b]pyridine (15.6 g, 132 mmol) in 400 mL tetrahydrofuran at −40° C. was added a suspension of N-bromosuccinimide in 120 mL tetrahydrofuran. Reaction mixture was warmed to room temperature and allowed to stir for 4 hours. Solid was filtered off. The reaction mixture was quenched with a sodium metabisulfite solution, and extracted with ethyl acetate. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was triturated with 1:1 hexane/ethyl acetate and filtered. The filtrate was concentrated and the trituration step was repeated three more times to afford a total of 25 g of the title compound, which was used without further purification. MS (DCI+) m/z 196.9 (M+H)+.

Provenance & Evidence