[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([NH2:12])=O)=[CH:4][CH:3]=1.C(#N)C.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]#[N:12])=[CH:6][CH:7]=1Add 2-(4-iodophenyl)benzamide (4.45 g, 0.0138 moles, preparation 56), acetonitrile (45 mL), and triethylamine (2.93 grams, 0.0289 moles) to a 100 mL 3-neck round-bottom flask equipped with a magnetic stirrer, internal temperature probe, ice-water bath, and addition funnel. Cool the contents of the 100 mL 3-neck round-bottom flask to 0° C. Add trifluoroacetic anhydride (3.04 grams, 0.0145 moles) to the reaction mixture via the addition funnel over 5 minutes. Observe a temperature increase to about 24° C., and cool the reaction mixture to 0° C. Stir the reaction mixture for 60 minutes. Add water (45 mL) and stir the suspension at ambient temperature for 60 minutes. Collect the precipitate by filtration and rinse the filter cake with water. Vacuum (15-25 mm) dry the filter cake at 50° C. to provide the title compound (4.03 g, 0.0132 moles) in 95.9% yield. 1H NMR(CDCl3, 500.0 MHz): δ 7.82 (app. d, 2H, J=9); 7.75 (dd, 1H, J=1.5, 8); 7.63 (dt, 1H, J=1.5, 7.5); 7.46 (d, 1H, J=8); 7.45 (dt, 1H, J=1.5, 7.5); 7.28 (app. d, 2H, J=8.5).
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