Methyl iodide → 6-Methoxy-1H-pyrrolo[2,3-b]pyridine

A mixture of 1H-pyrrolo[2,3-b]pyridin-6-ol (1.52 g, 11.4 mmol) and potassium carbonate (7.86 g, 57 mmol) in acetone (100 mL) was stirred under nitrogen at room temperature for 1 h. Iodomethane (2.6 g, 18.2 mmol) was added and the resulting mixture stirred at 56° C. for 12 h. The mixture was filtered, and the filtrate was concentrated to half its volume, diluted with water, and extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and evaporated. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 20% ethyl acetate/hexanes) to afford 6-methoxy-1H-pyrrolo[2,3-b]pyridine (0.5 g, 30%): LC/MS m/e calcd for C8H8N2O [M+H]+ 149.17, observed 149.1.

1. stirringthe resulting mixture stirred at 56° C. for 12 h
2. filtrationThe mixture was filtered
3. concentrationthe filtrate was concentrated to half its volume
4. additiondiluted with water
5. extractionextracted with dichloromethane
6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
7. customevaporated
8. customThe residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 20% ethyl acetate/hexanes)

ORD record

ord-2637bbeeb5e04698968ce4cd411c1d5e

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222416B2