[CH:1](=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].Br[C:18]1[CH:19]=[N:20][CH:21]=[C:22]([CH:25]=1)[C:23]#[N:24]>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>[C:23]([C:22]1[CH:25]=[C:18]([C:3]#[C:2][CH:1]=[C:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]2)[CH:19]=[N:20][CH:21]=1)#[N:24]A mixture of Compound 2b (0.5 g, 2.26 mmol), 5-bromonicotinonitrile (0.511 g, 2.26 mmol), bis(triphenylphosphine)palladium(II)dichloride (80 mg, 0.05 mmol), CuI (43.1 mg, 0.1 mmol) in anhydrous and degassed triethylamine (12.6 mL) was heated at 80° C. under a nitrogen atmosphere for 2 h in a sealed vessel. The reaction mixture was cooled, filtered on Celite, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether gradient from 4:96 to 30:70) affording the title product (0.731 g).
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