[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:16]=[N:17][CH:18]=[C:19](Br)[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C.[Cu]>[Br:14][C:15]1[CH:20]=[C:19]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:18]=[N:17][CH:16]=1
A mixture of 9H-carbazole (4.0 g, 24.1 mmol), 3,5-dibromopyridine (8.55 g, 36.1 mmol), copper powder (3.06 g, 48.2 mmol), potassium carbonate (13.3 g, 96.4 mmol) and 18-crown-6 (0.636 g, 2.4 mmol) in anhydrous DMF was degassed and heated at about 150° C. for about 40 hours. The crude mixture was then poured into water (200 mL), and then filtered. The solid was collected and dissolved in hot dichloromethane (500 mL) and an insoluble solid was then filtered off. The solution was absorbed on silica gel and purified by flash column (hexanes/ethyl acetate 12:1) to give a white solid product 2B (4.67 g, yield: 60%).
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