C([O-])([O-])=O.[Cs+].[Cs+].O=C1CCCCC1C(OCC)=O.[CH3:19][C:20]1[CH:21]=[CH:22][C:23](=[O:26])[NH:24][CH:25]=1.[F:27][C:28]1[CH:40]=[C:39](I)[CH:38]=[CH:37][C:29]=1[CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CS(C)=O.[Cu]I>[F:27][C:28]1[CH:40]=[C:39]([N:24]2[CH:25]=[C:20]([CH3:19])[CH:21]=[CH:22][C:23]2=[O:26])[CH:38]=[CH:37][C:29]=1[CH2:30][N:31]1[CH2:32][CH2:33][O:34][CH2:35][CH2:36]1A mixture of CuI (0.19 g, 1 mmol), Cs2CO3 (6.85 g, 20 mmol) and ethyl 2-oxocyclohexanecarboxylate (0.34 g, 2 mmol) in DMSO (10 mL) was stirred at rt for 30 min under N2. Then to the reaction mixture was added a solution of 5-methylpyridone (1.09 g, 10 mmol) and 4-(2-fluoro-4-iodobenzyl) morpholine (3.21 g, 10 mmol) in DMSO (12 mL) via syringe. The reaction mixture was heated at 100° C. overnight, cooled to rt and filtered. The filtrate diluted with H2O (50 mL) was extracted with CH2Cl2 (50 mL×3). The combined organic phases were concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1) to give the title compound as a white solid (0.70 g, 23%). The compound was characterized by the following spectroscopic data:
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