Hydrochloric Acid → 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

To a solution of 5-bromo-3-methyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridin (B-5-3) (5 g, 17.8 mmol) in THF (50 mL) was added 2 N HCl (20 mL). The mixture was stirred at reflux overnight. HPLC showed the reaction was complete. After the mixture was concentrated under reduced pressure, the residue was dissolved in aqueous NaHCO3 (20 mL) and extracted with EtOAc (10 mL×3). The organic layer was washed with saturated aqueous NaCl, dried over Na2SO4 and concentrated to give crude product, which was purified via prep. HPLC to give 5-bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine (B-5-4) (2 g, 53.2%) as a pale solid.

Provenance & Evidence