[H-].[Na+].[N+:3]([C:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)([O-:5])=[O:4].F[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.O>CN(C=O)C>[N+:3]([C:6]1[C:14]2[N:13]=[CH:12][N:11]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1)([O-:5])=[O:4]To a stirred suspension of sodium hydride (665 mg, 16.64 mmol) in DMF (90 mL) at rt was added 4-nitro-1H-benzimidazole (2714 mg, 16.64 mmol) in several portions. After stirring for 1 h, 4-fluorobenzonitrile (1350 mg, 11.146 mmol) was added and the mixture was stirred for 15 h at 130° C. After cooling, water was added, the precipitate was filtered off, washed with water and dried to yield 4-(4-nitro-benzoimidazol-1-yl)-benzonitrile (2.47 g, 47.76%).
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