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

To a solution of 5-bromopyridin-2(1H)-one (0.18 g, 1.03 mmol) in DMF (5 mL) was added iodomethane (0.2 mL, 3.1 mmol) and potassium carbonate (0.8 g, 6.2 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then concentrated under reduced pressure, the residue dissolved in ethyl acetate (200 mL), washed with water (50 mL) and brine solution. The organic layers were combined and dried over sodium sulfate, filtered and concentrated under vacuum to afford 5-bromo-1-methylpyridin-2(1H)-one [Albrecht, US Patent Application Publication No. 2009/0318436] as yellow solid (40 mg, 21%). 1H NMR (DMSO-d6): δ 8.01 (d, 1H), 7.49 (dd, 1H), 6.34 (d, 1H), 3.38 (s, 3H); LC-MS m/z calculated for [M+H]+ 187.96. found 188.2.

1. concentrationThe reaction mixture was then concentrated under reduced pressure
2. dissolutionthe residue dissolved in ethyl acetate (200 mL)
3. washwashed with water (50 mL) and brine solution
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under vacuum

ORD record

ord-c4aec1c9fad44487a535da81c4c6f48d

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266873B2