[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8](I)=[C:7]([NH2:12])[CH:6]=1)[CH3:2].[CH3:14][CH:15]([CH3:18])[C:16]#[CH:17]>C(N(CC)CC)C.[Cu]I.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>[NH2:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[C:17]#[C:16][CH:15]([CH3:18])[CH3:14])[C:4]([O:3][CH2:1][CH3:2])=[O:13]
To a solution of ethyl3-amino-4-iodobenzoate (Compound 31, 6.87 g, 23.1 mmol) in triethylamine (50 ml) at 25° C. under argon then added CuI (22 mg, 1.16 mmol), Pd(PPh3)2Cl2 (82 mg, 1.16 mmol), and 3-methyl-1-butyne ( 3.18 g, 46.2 mmol). The reaction was stirred for 20 h at 25° C., filtered off brown solid, and then rinsed solid with EtOAc, organic layer was concentrated in vacuo. The residue was purified by chromatography on silica gel (0→25% EtOAc-hexanes) to yield the title compound as a yellow solid.
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