Dimethylformamide → 5-Bromo-1-methylpyridin-2(1H)-one

With cooling with ice, potassium carbonate (5.96 g, 43.1 mmol) and methyl iodide (1.29 mL, 20.7 mmol) were added to a dimethylformamide (50 mL) solution of 5-bromo-2-hydroxypyridine (3.0 g, 7.24 mmol), and stirred at that temperature for 16 hours. Water was added to the reaction mixture, and extracted three times with ethyl acetate. The organic layer was washed with saturated brine, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, ethyl acetate/hexane=1/1) to obtain the entitled compound (2.92 g, 90%) as a colorless oil.

1. extractionextracted three times with ethyl acetate
2. washThe organic layer was washed with saturated brine
3. dry with materialdried with anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified through silica gel column chromatography (C-300, ethyl acetate/hexane=1/1)

ORD record

ord-6daffe007e33445a9ca00e428c54c0fd

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158652B2