[CH3:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([CH3:21])[C:3]=1[CH2:4][NH:5][C:6]1[C:14]2[NH:13][C:12]([CH3:15])=[N:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].[CH3:24]I>COCCOC.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([CH3:21])[C:3]=1[CH2:4][NH:5][C:6]1[C:14]2[C:10](=[N:11][C:12]([CH3:24])([CH3:15])[N:13]=2)[CH:9]=[CH:8][CH:7]=1
4-(2,6-Dimethyl-4-fluorobenzylamino)-2-methylbenzimidazole (0.1 g, 0.35 mmol) was dissolved in 1,2-dimethoxyethane (3 ml). Solid sodium hydroxide (25 mg, 0.63 mmol) and tetrabutylammonium bromide (5 mg, 0.016 mmol) were added. The mixture was stirred 15 minutes at ambient temperature. Methyl iodide (60 mg 0.42 mmol) was added and the reaction mixture was stirred at ambient temperature for 2.5 h. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using methylene chloride: ethyl acetate (50: 50) as eluent. 80 mg (76%) of the title compound was obtained.
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