Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][C@H:13]1[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]1)[CH:6]=[CH:5]2.[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C(C1CCCCC1=O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>[Cu]Cl.O.CN1CCCC1=O>[N:22]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([NH:12][C@H:13]2[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][CH2:14]2)[CH:6]=[CH:5]3)[CH:26]=[CH:25][N:24]=[CH:23]1
A mixture of (6-bromo-quinolin-2-yl)-(R)-indan-1-yl-amine (see example 53, step A) (339 mg, 1.0 mmol), commercially available imidazole (136 mg, 2.0 mmol), copper(I)chloride (10 mg, 0.1 mmol), 2-acetyl-cyclohexanone (35 mg, 0.25 mmol), potassium carbonate (145 mg, 1.05 mmol) and 1-methyl-2-pyrrolidone (1 ml) was heated in a sealed tube at 130° C. for 18 h. The reaction mixture was poured into water (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with saturated sodium bi-carbonate solution (2×20 ml) and brine (20 ml), dried (MgSO4) and evaporated. Further purification of the crude product by flash chromatography on silica gel (ethyl acetate/heptane) yielded the title compound (186 mg, 57%) as off-white foam.
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