Synthesis
Example 19: A mixture of 3-bromo-2-hydroxypyridine (740 mg, 4.25 mmol), potassium carbonate (1.18 g, 8.5 mmol), and iodomethane (2.65 mL, 42.5 mmol) in 1,2-dimethoxyethane (DME, 10 mL) was heated to reflux, and the reaction was carried out overnight. Upon completion of the reaction, the mixture was filtered and the solids were washed with ethyl acetate. The filtrate and washings were combined and concentrated to dryness under reduced pressure. The resulting crude product was purified by dry column chromatography on silica gel (27 g) to afford the target compound 3-bromo-1-methyl-2-pyridinone (0.63 g, 79% yield) using ethyl acetate as eluent. The product was detected by low resolution mass spectrometry (LRMS, electrospray ionization, positive ion mode) and showed a molecular ion peak m/z 188 ([M + H]+).
References
[1] Synlett, 2015, vol. 26, # 11, p. 1557 - 1562
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 23, p. 7076 - 7080
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4840 - 4860
[4] Patent: US6388084, 2002, B1
[5] Patent: WO2017/197046, 2017, A1. Location in patent: Page/Page column 344; 345
