Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(NCC)C.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>[Cu](I)I.CN(C=O)C>[CH3:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:42]#[C:41][Si:38]([CH3:40])([CH3:39])[CH3:37])[CH:3]=2)[N:8]=1In a sealed tube were introduced 6-bromo-2-methyl-quinoline (4.6 g, 21 mmol, 1 eq), PdCl2(PPh3)3 (727 mg, 1 mmol, 5% mol), copper iodide (197 mg, 1 mmol, 5% mol), and triphenylphosphine (1.1 g, 4.1 mmol, 20% mol). Then, DMF (35 mL) was added followed by diethylamine (6 mL, 62 mmol, 5 eq) and trimethylsilylacetylene (3.2 mL, 23 mmol, 1.1 eq). The mixture was refluxed overnight. After cooling down the solvent was evaporated and the crude product was purified by column chromatography (Florisil, Cyclohexane-AcOEt 95/5) and obtained as a white solid (4.2 g, 83%).
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