[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[C:23]2[C:22]([C:24]#[N:25])=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]([CH3:26])[CH:16]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:26][N:17]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([C:24]#[N:25])[C:23]=2[C:15]([N:10]2[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]2=[O:13])=[CH:16]1Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 110 mg, 0.621 mmol) was reacted with 3-bromo-1-methyl-1H-indole-4-carbonitrile (I-146b: 175 mg, 0.744 mmol), 1,4-dioxane (15 mL), copper iodide (11 mg, 0.0573 mmol), trans-1,2-diamino cyclohexane (21 mg, 0.1843 mmol) and potassium carbonate (171 mg, 1.239 mmol) to afford the crude product. Purification by column chromatography on silica gel (3% MeOH in CHCl3) afforded 49 mg of 1-Methyl-3-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-1H-indole-4-carbonitrile (23.90% yield).
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