Ethyl Acetate → 5-Bromo-2,3-dimethyl-1H-pyrrolo[2,3-B]pyridine

Participants

Reaction Steps

To a suspension of 5-bromo-2,3-dimethyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (B-6-3) (0.9 g, 2.5 mmol) in THF (30 mL) and MeOH (30 mL) was added aq. NaOH (20%, 19 mL) at room temperature. The mixture was heated to reflux overnight. TLC (Petroleum ether: EtOAc=5:1) showed the reaction was complete. After the solvent was removed under reduced pressure, water (20 mL) and CH2Cl2 (20 mL) were added into the mixture. The organic layer was separated, dried over anhydrous Na2SO4. The mixture was concentrated to give crude mixture which was purified via prep. HPLC to afford 5-bromo-2,3-dimethyl-1H-pyrrolo[2,3-b]pyridine (B-6-4) (0.4 g, 72.4%) as a white solid.

Provenance & Evidence