[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.O1CCCC1.C[Si](C)(C)[C:17]([F:20])([F:19])[F:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O.[Cl-].[Na+].O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:6]([OH:7])[C:17]([F:20])([F:19])[F:18])=[CH:8][CH:9]=16-Chloronicotinaldehyde (500 mg, 3.53 mmol) was added to tetrahydrofuran (23 mL) and cooled to 0° C. Trimethyl(trifluoromethyl)silane (0.66 mL, 4.24 mmol) was added followed by 1 M tetra-n-butylammonium fluoride in tetrahydrofuran (4.24 mL, 4.24 mmol). The reaction mixture was allowed to warm to room temperature over 1 hour. The reaction was then diluted with water and brine and extracted with ethyl acetate three times. The organic layers were combined and dried over magnesium sulfate, filtered, and concentrated in vacuo. The concentrated material was purified via silica gel chromatography (0-40% ethyl acetate in hexanes) to afford the title compound.
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