[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.Cl[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].CN1CCCC1=O>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH:9]=2)=[CH:4][CH:3]=13-(4-Fluorophenyl)-1H-indole 1a (39.3 g), 4-chloropyridine hydrochloride (55.8 g), K2CO3 (102.8 g), CuBr (15 g) and N-methylpyrrolidinone (1.2 l) were refluxed under stirring for 18 h. The reaction mixture was cooled, poured into water (1.0 l) and extracted with diethyl ether (2×1 l). The combined organic phases were washed with brine (3×1.5 l), dried (Na2SO4) and treated with activated carbon. Evaporation of the solvent gave the title compound which was crystallized from diethyl ether. Yield: 42.0 g, mp 115°-118° C.
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