3-Bromo-5-methylpyridine → 1-(5-Methylpyridin-3-yl)ethan-1-one

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To 3-bromo-5-methylpyridine 1-1 (2 g, 11.63 mmol) in diethyl ether (30 ml) at −78° C. was added uLi (8.72 ml, 13.95 mmol) dropwise. After 30 min, N-methoxy-N-methylacetamide n-BuLi was added. The resulting mixture was stirred at −78° C. for 2 h then at rt overnight, quenched with saturated NH4Cl solution and diluted with EtOAc. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give a yellow residue, which was purified by column chromatography (0-65% EtOAc in hexane) to give the desired product 1-2: 1H NMR (400 MHz, CDCl3) δ 8.98 (s, 1H), 8.62 (s, 1H), 8.04 (s, 1H), 2.63 (s, 3H), 2.41 (s, 3H).

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