A mixture of ethyl{(4-bromobenzyl)[4-(trifluoromethyl)benzyl]amino}(oxo)acetate (100 mg, 0.23 mmol), 1-tetradecyne (66 mg, 0.34 mmol), copper(I) bromide (4.5 mg, 0.031 mmol) and palladium tetrakis(triphenylphosphine) (11 mg, 0.0095 mmol) in Et3N (1 mL) was heated at 90° C. for 75 min. After cooling to rt, the reaction mixture was diluted with an aqueous HCl solution (1N, 10 mL) and extracted with Et2O (2×20 mL). The combined organic layers were dried over MgSO4 and the solvent was removed under reduce pressure. The residue was purified by flash chromatography (cyclohex./Et2O 4:1) to give the title compound as yellow oil (63 mg, 50%). 1H NMR (CDCl3, 300 MHz) δ 7.61 (m, 2H), 7.33 (m, 4H), 7.14 (m, 2H), 4.51 (s, 1H), 4.47 (s, 1H), 4.34 (m, 4H), 2.40 (m, 2H), 1.58-1.26 (m, 23H), 0.88 (m, 3H). HPLC (Condition A), Rt: 8.21 min (HPLC purity: 99.3%).
