Methyl iodide → 4-Bromo-1-methylpyridin-2(1H)-one

To a solution of 4-bromo-2-hydroxypyridine (0.10 g, 0.57 mmol) in THF (5.0 mL) was added, portion wise, NaH (60% dispersion in mineral oil, 0.02 g, 0.86 mmol). The resulting solution was stirred at room temperature for 5 min followed by addition of methyl iodide (0.11 mL, 1.72 mmol). The reaction mixture was then allowed to stir overnight at room temperature. After the completion of reaction, THF was distilled off, added water and extracted with ethyl acetate (3×25 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated to obtain the desired product (0.10 g, 92%). 1H NMR (DMSO-d6, 400 MHz): δ 3.43 (s, 3H), 6.45 (dd, J=2.40 and 7.20 Hz, 1H), 6.69 (d, J=2.40 Hz, 1H) and 7.68 (d, J=7.20 Hz, 1H). MS: 188.05 (M+H+).

1. stirringto stir overnight at room temperature
2. distillationwas distilled off
3. additionadded water
4. extractionextracted with ethyl acetate (3×25 mL)
5. washThe combined organics was washed with water, brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-b68944e3550f43bfa9509ff105b8d939

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299065B2