Synthesis
In a dry Schlenk test tube, 2-bromo-6-hydroxypyridine (3.43 g, 31.44 mmol) was dissolved in 50 mL of 1,4-dioxane and KOt-Bu (8.69 g, 62.88 mmol) was added. The reaction mixture was stirred at 100 °C for 2 h and subsequently cooled to room temperature. Iodomethane (19.6 mL, 314.41 mmol) was added dropwise and the mixture was stirred at 80 °C for 16 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was partitioned between dichloromethane (DCM) and water. Extraction was carried out using DCM (3 times) and the organic phases were combined and dried over anhydrous magnesium sulfate (MgSO4). After filtration, the solvent was evaporated to obtain the crude product. Purification by column chromatography (eluent: 5% methanol in DCM solution) afforded 6-bromo-1-methylpyridin-2(1H)-one (orange solid, 3.70 g, 96% yield).
References
[1] Synlett, 2015, vol. 26, # 11, p. 1557 - 1562
[2] Patent: US2017/313683, 2017, A1. Location in patent: Paragraph 0412
[3] Patent: WO2015/92713, 2015, A1. Location in patent: Page/Page column 323
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 23, p. 7076 - 7080
