C(CC(=O)C)(=O)C.O.[NH3:9].Br[C:11]1[CH:12]=[C:13]([CH3:29])[C:14]([C:17]2[CH2:22][CH2:21][CH:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH2:19][CH:18]=2)=[N:15][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O.[Cu]>[CH3:29][C:13]1[CH:12]=[C:11]([NH2:9])[CH:16]=[N:15][C:14]=1[C:17]1[CH2:22][CH2:21][CH:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH2:19][CH:18]=1Acetylacetone (0.31 ml) and 28% ammonia water (1.78 ml) were added to a suspension of 4-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]morpholine (2 g), copper acetylacetonate (466 mg) and cesium carbonate (3.86 g) in N,N-dimethylformamide (12 ml), sealed in a tube under nitrogen atmosphere and stirred at 100° C. for 20 hours. After completion of the reaction, the reaction solution was left stand to room temperature and concentrated. The resulting residue was diluted with water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (chlorofolin/methanol) to give the titled compound (1.31 g) as a pale yellow solid.
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