[C:1]1([NH:7][C:8]2[CH:20]=[CH:19][C:11]3[O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:10]=3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[CH:20]=[CH:19][C:11]3[O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:10]=3[CH:9]=2)=[CH:24][CH:23]=1N-phenyldibenzo[b,d]furan-2-amine (5.0 g, 19.3 mmol), and 1-bromo-4-iodobenzene (10.9 g, 38.6 mmol) were mixed in 100 mL of toluene. The solution was bubbled with nitrogen for 15 min. Pd(OAc)2 (0.22 g, 1.0 mmol), triphenylphosphine (0.51 g, 1.9 mmol) and sodium t-butoxide (2.2 g, 23.1 mmol) were added. The mixture was refluxed overnight under nitrogen.
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