Cesium fluoride → 2-(Bromomethyl)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridine

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To a solution of 9 (5.6 g, 21 mmol) in DMF (100 mL) was added 1,2-dibromotetrafluoroethane (10 g, 42 mmol) and CsF (6.4 g, 42 mmol). The reaction was allowed to stir at room temperature for 3 h, and the resulting purple solution was concentrated and loaded directly on flash column chromatography (EtOAc/hexanes, 1:19-1:9) to give 6 (5.7 g, 20.8 mmol, 99%) as a pale yellow oil: 1H NMR (500 MHz, CDCl3) δ 2.19 (s, 6H), 2.47 (s, 3H), 4.56 (s, 2H), 5.93 (s, 2H), 7.01 (s, 1H), 7.30 (s, 1H); 13C NMR (125 MHz, CDCl3) δ 13.3, 21.1, 33.5, 107.1, 121.8, 122.9, 128.5, 150.7, 151.7, 156.3; LCQ-MS (M+H+) calcd for C13H16BrN2 279. found 279; LC-TOF-MS (M+H+) calcd for C13H16BrN2 279.04969. found 279.04963.

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