Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[C:19]1([C:25]#[CH:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCOC(C)=O.CCCCCC>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:19]1([C:25]#[C:26][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1After 2-chloroquinoline (29.7 mg, 0.182 mmole) was dissolved in THF (1.5 mL), PdCl2(PPh3)2 (2.6 mg, 0.0037 mmole), and CuI (1.5 mg, 0.0063 mmol) were added thereto and stirred for 5 min under nitrogen atmosphere. To the resulting mixture triethylamine (0.15 mL) and phenylacetylene (0.03 mL, 0.273 mmol) were successively added, followed by stirring at 80° C. for 24 hr after sealing. The completion of the reaction was confirmed by TLC (EtOAc/Hexane=1:10). When the reaction was completed, the reactant was filtered through Celite and extracted with a mixture of EtOAc and H2O, to thereby separate an organic layer. The organic layer was dried over anhydrous MgSO4, concentrated under reduced pressure, and purified by column chromatography (EtOAc/Hexane=1:10, R.f: 0.35), to thereby obtain 2-(phenylethynyl)quinoline (24.9 mg, 60%) as a brown solid.
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