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

Participants

Reaction Conditions

Reaction Steps

1H-Pyrrolo[2,3-b]pyridine (8.78 g, 74.3 mmol) and 5% palladium-carbon in a mixture of triethylamine (5 mL) and formic acid (30 mL) was stirred at 80° C. for 4 days. The reaction mixture was allowed to cool to room temperature and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was adjusted to pH 12 with 6 M aqueous sodium hydroxide and stirred at 65° C. for 5 hours. The reaction mixture was allowed to cool to room temperature and extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2-ethyl acetate/methanol=20/1 (v/v)) to give the title compound as a pale yellow solid (2.15 g, yield 24%).

Provenance & Evidence