Methyl iodide → 3-Bromo-1-methyl-5-(trifluoromethyl)pyridin-2(1H)-one

To a solution of 3-bromo-2-hydroxy-5-(trifluoromethyl)pyridine (1.0097 g, 4.1724 mmol) in chloroform (20 mL) was added silver carbonate (1.1964 g, 4.3388 mmol) and methyl iodide (0.40 mL, 6.4 mmol). The reaction mixture was stirred at room temperature for two hours and then at 40° C. for 24 hours. Additional methyl iodide (0.40 mL, 6.4 mmol) was added and the reaction kept at 40° C. for an additional 15 hours. The reaction mixture was then diluted with dichloromethane, filtered through celite, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (0 to 80% ethyl acetate in heptanes) to yield 0.5297 g (50%) of 3-bromo-1-methyl-5-(trifluoromethyl)pyridin-2(1H)-one. 1H NMR (400 MHz, DMSO-d6) δ: 8.47 (d, J=0.9, 1H), 8.22 (d, J=2.5, 1H), 3.56 (s, 3H).

1. waitat 40° C. for 24 hours
2. waitthe reaction kept at 40° C. for an additional 15 hours
3. filtrationfiltered through celite
4. customevaporated in vacuo
5. customThe crude product was purified via flash chromatography on silica gel (0 to 80% ethyl acetate in heptanes)

ORD record

ord-84fb1b371aba4c61a12ccbbb14d583d9

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999998B2