Methyl iodide → 5-Bromo-1-methylpyridin-2(1H)-one

Temperature

0 °C

5-Bromopyridin-2(1H)-one (2.00 g, 11.5 mmol) was added in portions to a mixture of sodium hydride (1.10 g, 27.5 mmol) in THF (100 mL) at 0° C. The mixture was stirred for 1 h at 0° C. followed by addition of iodomethane (8.20 g, 57.5 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched with water (2 mL) and then concentrated. The residue was suspended in water (50 mL) and the resulting mixture was extracted with EtOAc (50 mL×3). The organic extracts were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was washed with petroleum ether (30 mL) and dried to afford 5-bromo-1-methylpyridin-2(1H)-one (1.7 g, 79% yield) as a yellow solid.

1. temperatureto warm to ambient temperature
2. stirringstirred overnight
3. customThe reaction was quenched with water (2 mL)
4. concentrationconcentrated
5. extractionthe resulting mixture was extracted with EtOAc (50 mL×3)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated
8. washThe residue was washed with petroleum ether (30 mL)
9. customdried

ORD record

ord-2662d34a63c14e0cb1211e44b082b411

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434761B2