[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.[CH2:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:13]#[CH:14]>N1CCCCC1.[Cu]I>[C:18]([O:17][C:16]([NH:15][CH2:12][C:13]#[C:14][C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:11])=[CH:5][CH:6]=1)=[O:22])([CH3:21])([CH3:20])[CH3:19]Methyl-4-iodobenzoate (1.5 g, 5.7 mmol) and t-butyl prop-2-ynylcarbamate (0.89 g, 5.7 mmol, reference example 82) are dissolved in piperidine (12 mL) and this solution purged with nitrogen. Copper(I) iodide (22 mg, 0.11 mmol) and dichlorobis(triphenylphosphine) palladium (40 mg, 0.057 mmol) is added and the mixture is stirred at R.T. After 2 hours, the solvent is removed in vacuo and the residue added to CH2Cl2 and washed with 1N HCl, water and brine, then dried over magnesium sulfate. The solvent is removed in vacuo and the residue purified by flash chromatography, eluting with 20% ethyl acetate/hexane to provide the title compound as a white solid (1.1 g, 67% yield): 1H NMR (300 MHz, CDCl3) d 7.98 (d, 2H), 7.48 (d, 2H), 4.79 (bs, 1H), 4.17 (d, 2H), 3.91 (s, 3H), 1.48 (s, 9H).
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