[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:13])[CH3:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH:23]=O)=[CH:15]1.N1CCCCC1>C(O)C>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11](=[O:13])/[CH:12]=[CH:23]/[C:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:14][CH:15]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=13',5'-Dimethoxyacetophenone (1.10 g) and indole-3-carboxaldehyde (1.45 g) were dissolved in ethanol (20 ml), and piperidine (0.85 g) was added thereto, followed by heating under reflux for 32 hours. The reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration, followed by recrystallization from ethanol to give Compound 69 (1.79 g).
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