[CH3:1][C:2]1[C:3](=[O:9])[NH:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:10][C:11]1[CH:23]=[C:22](I)[CH:21]=[CH:20][C:12]=1[CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>[Cu]I.CN(C=O)C>[F:10][C:11]1[CH:23]=[C:22]([N:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]2=[O:9])[CH:21]=[CH:20][C:12]=1[CH2:13][N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1A mixture of 3,5-dimethylpyridin-2(1H)-one (0.22 g, 1.80 mmol), 4-(2-fluoro-4-iodobenzyl)morpholine (0.58 g, 1.80 mmol), K2CO3 (2.48 g, 18 mmol), CuI (0.02 g, 0.1 mmol) and DMF (3 mL) was refluxed under N2. The reaction process was monitored by TLC. The reaction mixture was cooled to rt and filtered. To the filtrate was added H2O (10 mL) and CH2Cl2 (20 mL). The CH2Cl2 layer was separated, and the aqueous layer was extracted with CH2Cl2 (20 mL×2). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a white solid (0.28 g, 50%). The compound was characterized by the following spectroscopic data:
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