[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[N:16]=1>CN(C)C=O.[Cu]I>[S:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[CH2:22][O:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[N:16]=1
To a solution containing meta-trifluoromethylphenol (3.62 g, 0.0045×5.0 mol), sodium hydride (0.36 g, (Ca.60% in mineral oil), 0.0045×2.0 mol) and CuI (0.42 g, 0.0045×0.5 mol) in dimethylformamide, 2-chloro-6-(2-thienylmethyloxy)pyridine (1.0 g, 0.0045 mol) was added and the resultant solution was refluxed for about 3 hours. Additional sodium hydride (0.36 g, (60% in mineral oil), 0.0045×2.0 mol) was added thereto and the resultant solution was refluxed for another about 1 hour, thereafter the reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate. The obtained organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and thereafter, concentrated and purified on a silica gel column to obtain the end product.
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