Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]3[CH2:12][CH2:11]3)[N:7]([CH3:13])[C:6]=2[CH:14]=1.[O:15]=[C:16]1[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][NH:17]1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.O1CCOCC1>[CH:10]1([C:8]2[N:7]([CH3:13])[C:6]3[CH:14]=[C:2]([N:17]4[CH:18]=[CH:19][C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:21][C:16]4=[O:15])[CH:3]=[CH:4][C:5]=3[N:9]=2)[CH2:12][CH2:11]1
To a mixture of 6-bromo-2-cyclopropyl-1-methyl-1H-benzimidazole (984 mg), methyl 2-oxo-1,2-dihydropyridine-4-carboxylate (600 mg), potassium carbonate (1.08 g) and dioxane (25 ml) were added CuI (298 mg) and trans-N,N′-dimethylcyclohexane-1,2-diamine (223 mg), and the mixture was heated at 80° C. for 12 h. The mixture was concentrated in vacuo, and diluted with DCM. The mixture was washed with brine, dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (MeOH/DCM) to give the title compound (800 mg) as a white solid.
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