I[C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)CC)C.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:2]2[CH:9]=[N:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:20][CH:19]=1To a solution of 3-iodo-isonicotinonitrile (911 mg, 3.96 mmol) in DMF (10 ml) are added bis(triphenylphosphine)-palladium(II)-chloride (139 mg, 0.20 mmol), copper(I) iodide (22.6 mg, 0.12 mmol), triethylamine (1.10 ml, 7.9 mmol) and 1-bromo-4-ethynyl-benzene (716 mg, 3.96 mmol). The mixture is flushed with nitrogen, heated to 80° C. and stirred in a closed reaction vial at this temperature for 18 hours. The reaction mixture is allowed to cool to room temperature and partitioned between dichloromethane and 1 N HCl. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 3-(4-bromo-phenylethynyl)-isonicotinonitrile as beige solid; HPLC/MS 2.13 min (A), [M+H] 283/285.
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