Methyl iodide → 5-Bromo-1,4-dimethyl-1,2-dihydropyridin-2-one

Temperature

0 °C

To a solution of 5-bromo-4-methylpyridin-2-ol (1.12 g, 6.0 mmol) in anhydrous THF (20 mL) was added NaH (288.0 mg, 12.0 mmol) and the reaction mixture was stirred at 0° C. for 30 min. Then, methyl iodide (1.7 g, 12.0 mmol) was added and stirred at room temperature for 3 h. Saturated NH4Cl (100 mL) was added and the resulting mixture was extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel (PE:EA=10:1 to 2:1) to give the title compound (1.0 g, 83.3%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 7.44 (s, 1H), 6.94 (s, 1H), 3.51 (s, 3H), 2.24 (s, 3H). LCMS (M+H)+ 1202.

1. stirringstirred at room temperature for 3 h
2. extractionthe resulting mixture was extracted with ethyl acetate (100 mL×3)
3. washThe combined organic layers were washed with brine (100 mL)
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated
6. customThe residue was purified by column chromatography on silica gel (PE:EA=10:1 to 2:1)

ORD record

ord-becee13058aa458b9b7a33d7b1c125e5

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034900B2