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

Temperature

80 °C

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%).

1. temperatureto cool to room temperature
2. filtrationfiltered
3. concentrationthe filtrate was concentrated under reduced pressure
4. stirringstirred at 65° C. for 5 hours
5. temperatureto cool to room temperature
6. extractionextracted with chloroform
7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2-ethyl acetate/methanol=20/1 (v/v))

ORD record

ord-1ae2ef5275a74aa3a2bd034fc1704aee

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216999B2