[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[N:4]=1)#[CH:2].Br[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15].C(N(CC)CC)C.O>CN(C)C=O>[CH3:9][C:5]1[N:4]=[C:3]([C:1]#[C:2][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])[CH:8]=[CH:7][CH:6]=1A mixture of 1 g (8.54 mMol) 2-ethynyl-6-methyl-pyridine (prepared in analogy to D. E. Ames et al., Synthesis, 1981, p. 364-5), 2.3 g (12.8 mMol) 3-bromo-benzonitrile, 0.47 g (0.7 mMol) bis-(triphenylphosphine)-palladium-II-chloride, 80 mg (0.41 mMol) cuprous iodide and 1.53 ml (15 mMol) triethylamine in 10 ml dimethylformamide is stirred for 3 hours at 90° C. The reaction mixture is cooled to ambient temperature, poured into water and extracted with dichloromethane. The organic layer is dried over sodium sulfate, filtered, evaporated to dryness and the residue is purified by chromatography on silica gel with hexane/ethyl acetate (4:1) as eluant. Crystallization from hexane of the obtained product affords 0.53 g (28.4%) of the title compound as brown crystals, melting point 120-3° C.
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