[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[O:16][C:17]([F:20])([F:19])[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:28]1([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][C:12]([N:31]2[CH2:30][CH2:29][N:28]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32]2)=[CH:11][C:10]=1[O:16][C:17]([F:20])([F:19])[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1A mixture of the product of EXAMPLE 45A (7.92 g, 18.21 mmol), tert-butyl piperazine-1-carboxylate (3.73 g, 20 mmol), palladium diacetate (205 mg, 0.91 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (850 mg, 1.36 mmol) and cesium carbonate (11.88 g, 36 mmol) in toluene (200 mL) was heated under nitrogen at 100° C. for 20 hours. After cooling to ambient temperature, the mixture was concentrated and the residue was diluted with dichloromethane (300 mL), washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 10/1 petroleum ether/ethyl acetate to give the title compound. MS: 542 (M+H+).
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