C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[C:48]1[CH:53]=[CH:52][C:51]([NH:54][C:55]2[CH:60]=[CH:59][C:58]([O:61][C:62]3[C:71]4[C:66](=[CH:67][C:68]([O:74][CH3:75])=[C:69]([O:72][CH3:73])[CH:70]=4)[N:65]=[CH:64][CH:63]=3)=[CH:57][CH:56]=2)=[CH:50][CH:49]=1.[NH:76]1[CH2:81][CH2:80][O:79][CH2:78][CH2:77]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:73][O:72][C:69]1[CH:70]=[C:71]2[C:66](=[CH:67][C:68]=1[O:74][CH3:75])[N:65]=[CH:64][CH:63]=[C:62]2[O:61][C:58]1[CH:59]=[CH:60][C:55]([NH:54][C:51]2[CH:52]=[CH:53][C:48]([N:76]3[CH2:81][CH2:80][O:79][CH2:78][CH2:77]3)=[CH:49][CH:50]=2)=[CH:56][CH:57]=1Palladium acetate (18 mg) and (+)-BINAP (70 mg) were dissolved in toluene (1.5 ml), and the solution was stirred at room temperature for 5 min. (4-Bromophenyl)-[4-(6,7-dimethoxy-4-quinolyloxy)phenyl]amine (100 mg), morpholine (0.15 ml), and cesium carbonate (200 mg) were added in that order to the reaction solution, and the mixture was stirred at 80° C. overnight. The insolubles were removed by filtration, and the solvent was then removed by evaporation under the reduced pressure. The residue was purified by thin-layer chromatography on silica gel using chloroform/acetone to give the title compound (10 mg, yield 9%).
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