C(N(CC)CC)C.[CH3:8][C:9]1[N:13]([CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([C:23]3[S:24][CH:25]=[C:26]([C:28]#[C:29][Si](C)(C)C)[N:27]=3)[CH2:19][CH2:18]2)=[O:16])[N:12]=[C:11]([C:34]([F:37])([F:36])[F:35])[CH:10]=1.Br[C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:46][O:45][C:42]1[CH:43]=[CH:44][C:39]([C:29]#[C:28][C:26]2[N:27]=[C:23]([CH:20]3[CH2:21][CH2:22][N:17]([C:15](=[O:16])[CH2:14][N:13]4[C:9]([CH3:8])=[CH:10][C:11]([C:34]([F:36])([F:35])[F:37])=[N:12]4)[CH2:18][CH2:19]3)[S:24][CH:25]=2)=[CH:40][CH:41]=1Tetrakis(triphenylphosphine)palladium(0) (25 mg), copper(I) iodide (8 mg) and triethylamine (53 mg) are added to a solution of 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(trimethylsilyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (I-98, 200 mg) and 1-bromo-4-methoxybenzene (91 mg) in degassed N,N-dimethylformamide (2 ml). After warming to 85° C., tetra-n-butylammonium fluoride (1M in THF, 0.48 ml) is added dropwise. The reaction mixture is then diluted with water and extracted with ethyl acetate. The organic extracts are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives 1-(4-{4-[(4-methoxyphenyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (84 mg).
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