C(N(CC)CC)C.[C:8]([C:10]1[N:11]=[C:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:33])[CH2:22][N:23]3[C:27]([CH3:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[N:24]3)[CH2:17][CH2:16]2)[S:13][CH:14]=1)#[CH:9].I[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41][CH3:42]>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>[CH3:42][O:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[C:9]#[C:8][C:10]1[N:11]=[C:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:33])[CH2:22][N:23]3[C:27]([CH3:28])=[CH:26][C:25]([C:29]([F:30])([F:32])[F:31])=[N:24]3)[CH2:17][CH2:16]2)[S:13][CH:14]=1Tetrakis(triphenylphosphine)palladium(0) (25 mg), copper(I) iodide (7 mg) and triethylamine (48 mg) are added to a solution of 1-[4-(4-ethynyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (I-86, 150 mg) and 1-iodo-2-methoxybenzene (101 mg) in degassed N,N-dimethylformamide (1.5 ml). After 2 hours of stirring at 85° C., 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-[(2-methoxyphenyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (100 mg).
Wird geladen…