Dimethylformamide → 3-Bromo-1-methylpyridin-4(1H)-one

To a solution of 3-bromo-4-pyridinol (308.2 mg, 1.771 mmol) in N,N-dimethylformamide (10 mL, 100 mmol) was added potassium carbonate (371.0 mg, 2.684 mmol) and methyl iodide (133 uL, 2.14 mmol). The reaction was stirred at room temperature for 18 hours. The reaction mixture was filtered and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (12 g silica, solvent gradient: 0-20% methanol in dichloromethane) to yield 269.9 mg (81%) of 3-bromo-1-methylpyridin-4(1H)-one. LCMS (ESI): M+H=188.2; 1H NMR (400 MHz, DMSO-d6) δ 8.24 (d, J=2.1 Hz, 1H), 7.68 (dd, J=7.4, 2.1 Hz, 1H), 6.21 (d, J=7.4 Hz, 1H), 3.65 (s, 3H).

1. filtrationThe reaction mixture was filtered
2. customevaporated in vacuo
3. customThe crude product was purified via flash chromatography on silica gel (12 g silica, solvent gradient: 0-20% methanol in dichloromethane)

ORD record

ord-b18e9eaa2d5247f7ba0225433d3544a3

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623889B2