[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[CH3:22]I.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:22])[C:14](=[O:19])[C:15]([F:17])([F:18])[F:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]Add 20.0 9 (0.07 mol) of N-[2-(3,4-dimethoxyphenyl)ethyl]trifluoroacetamide to a suspension of 3.17 g (0.08 mol) of 60% sodium hydride in 50 mL of dry tetrahydrofuran. Stir this suspension for 30 minutes at room temperature. After 30 minutes, add 6.72 mL (0.11 mol) of methyl iodide and stir at room temperature for one h. After one h, filter reaction mixture and make basic (pH=14) with 4N sodium hydroxide. Wash this mixture with 2×100 mL of water. Extract the combined aqueous washes with 2×100 mL of methylene chloride. Wash the combined organic extracts with 6N hydrochloric acid, then with 100 mL of water. Dry the organic layer over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo to provide the title compound.
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