[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)[CH3:2].C(N(CC)CC)C.C(O)=O>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=1)[CH3:2]Pd/C (5 g, 10%) was added to a solution of 3-(4-cyanophenyl)acrylic acid ethyl ester (50 g, 0.25 mol; see step (i) above) in dry ethyl acetate (500 mL) under a nitrogen atmosphere, followed by triethylamine (50.3 g, 0.5 mol) and formic acid (57.2 g, 1.24 mol). The mixture was refluxed overnight under a nitrogen atmosphere. After the completion of the reaction (monitored by TLC), the mixture was filtered and the filtrate then washed with water, 5% NaHCO3 solution and brine, before being dried over sodium sulfate. Solvent evaporation under reduced pressure yielded 50 g (99%) of the sub-title compound as a pale yellow oil.
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