[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([S:11][C:12]([F:15])([F:14])[F:13])[CH:10]=[C:5]2[N:4]=[CH:3]1.Br[C:17]1[CH:22]=[CH:21][C:20]([S:23][C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=1[S:28][CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(OCC)(=O)C>[CH2:29]([S:28][C:18]1[CH:19]=[C:20]([S:23][C:24]([F:27])([F:25])[F:26])[CH:21]=[CH:22][C:17]=1[C:3]1[N:2]([CH3:1])[C:6]2=[N:7][CH:8]=[C:9]([S:11][C:12]([F:13])([F:15])[F:14])[CH:10]=[C:5]2[N:4]=1)[CH3:30]A mixture of 0.11 g of 3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine, 0.15 g of 1-bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene, 0.01 g of palladium(II) acetate, 0.01 g of triphenylphosphine, 0.02 g of copper(II) acetate monohydrate, 0.13 g of potassium carbonate and 3 ml of toluene was stirred under heating and refluxing for 2 hours. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered. The filtrate was extracted with ethyl acetate, and then dried over anhydrous sodium sulfate. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.20 g of 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound 7).
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