[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>[Cu].CN(C)C=O>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([N:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)=[CH:23][CH:22]=2)=[CH:19][CH:20]=1
A mixture of carbazole (300 mg, 1.81 mmol), 4,4′-dibromobiphenyl (846 mg, 2.71 mmol), copper (344 mg, 5.43 mmol), 18-crown-6 (187 mg, 0.71 mmol), potassium carbonate (750 mg, 5.43 mmol), and anhydrous N,N-dimethylformamide (10 mL) was degassed for 30 minutes. The mixture was heated to 155° C. for 66 hours under argon. After cooling, the mixture was poured into DCM (400 mL) and the subsequent mixture was filtered. The filtrate was loaded on silica gel. A flash column (silica, 10% DCM in hexane) and reprecipitation in DCM/hexanes yielded 304 mg (42% yield) of pure product; confirmed by HNMR.
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