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 (1.0 g, 8.46 mmol) and 10% palladium-carbon (500 mg) were dissolved in a mixture of formic acid (10 mL) and triethylamine (10 mL), and the solution was stirred at 70° C. for 17 hours. To this reaction mixture was further added 10% palladium-carbon (270 mg), and the mixture was stirred at 70° C. for 2 hours. The reaction mixture was cooled to room temperature, then an aqueous solution of 5N sodium hydroxide was added thereto, the solution was extracted with ethyl acetate and tetrahydrofuran, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1), and 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (614 mg, 5.11 mmol, 60%) was obtained as a pale yellow solid.

Provenance & Evidence