[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Br:10])[CH:9]=1)(=[O:3])[CH3:2].C[Si](C)(C)[C:13]([F:16])([F:15])[F:14].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O.ClCCl>[Br:10][C:8]1[CH:9]=[C:4]([C:1]([OH:3])([CH3:2])[C:13]([F:16])([F:15])[F:14])[CH:5]=[N:6][CH:7]=1
To a solution of 3-acetyl-5-bromopyridine (0.20 g, 1.0 mmol) in tetrahydrofuran (3.3 mL) were added a solution of trimethyl(trifluoromethyl)silane in tetrahydrofuran (0.5 M, 4.0 mL, 2.0 mmol) and a solution of tetrabutylammonium fluoride in tetrahydrofuran (1.0 M, 0.1 mL, 0.1 mmol). The resulting reaction mixture was stirred at room temperature for 1 h, then diluted with water and dichloromethane. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0 to 6% dichloromethane in acetone) provided the title compound: LCMS m/z 271.75 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.71 (s, 1 H), 8.68 (s, 1 H), 8.11 (s, 1 H), 3.12 (br s, 1 H), 1.82 (s, 3H).
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