83004-13-1

At -80 °C, 2-bromo-6-methylpyridine (CAS 5315-25-3) (2.0 g, 11.7 mmol, 1.0 eq.) was dissolved in THF (10 mL) and LDA (12.3 mL, 12.3 mmol, 1.05 eq.) was added slowly. The reaction mixture was kept stirred at -78 °C for 1 hour. Subsequently, iodomethane (1.8 g, 12.3 mmol, 1.05 eq.) was added to the reaction system and the mixture was gradually warmed up to room temperature and stirring was continued for 3 hours. Upon completion of the reaction, the reaction was quenched with saturated NaHCO3 solution (2 mL), diluted with water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The organic phases were combined, washed with brine and dried over anhydrous Na2SO4. After concentration under reduced pressure, the residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate (20/1) as eluent to afford 2-bromo-6-ethylpyridine (1.0 g, yellow solid, 46% yield). The product was detected by ESI-MS and showed (M + H)+ peaks located at 185.9 and 187.9.

[1] Patent: US2009/253750, 2009, A1. Location in patent: Page/Page column 9
[2] Patent: WO2016/11390, 2016, A1. Location in patent: Page/Page column 194
[3] Patent: WO2017/127430, 2017, A1. Location in patent: Page/Page column 52
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 3, p. 501 - 507