[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH2:11][CH2:12][CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:7]([CH2:9]Cl)=[N:8][C:4]=2[CH:3]=1.[CH3:20][S:21]([C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)(=[O:23])=[O:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH2:11][CH2:12][CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:7]([CH2:9][N:26]3[C:27]4[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:24]([S:21]([CH3:20])(=[O:22])=[O:23])=[CH:25]3)=[N:8][C:4]=2[CH:3]=1A mixture of 5-chloro-2-(chloromethyl)-1-(3-(methylsulfonyl)propyl)-1H-benzo[d]imidazole (120 mg, 0.37 mmol) and 3-(methylsulfonyl)-1H-indole (72 mg, 0.37 mmol) in DMF (3 mL) was treated with K2CO3 (104 mg, 0.74 mmol) at RT. The reaction solution was stirred at RT for overnight. The solid was filtered off and the filtrate was purified by prep-HPLC to give 5-chloro-2-{[3-(methylsulfonyl)-1H-indol-1-yl]methyl}-1-[3-(methylsulfonyl)propyl)-1H-benzimidazole (100 mg, yield: 78%) as off-white solid.
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