[C:1]([O:5][C:6](=[O:18])/[CH:7]=[C:8](\[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)/[CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:19](#[N:22])[CH2:20][CH3:21].FC1C=CC(NC(=O)C)=CC=1>CC([O-])=O.CC([O-])=O.[Cu+2]>[C:1]([O:5][C:6]([C:7]1[C:19]([CH2:20][CH3:21])=[N:22][N:10]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[C:8]=1[CH3:9])=[O:18])([CH3:2])([CH3:3])[CH3:4]According to AVV A, (Z)-3-(4-fluorophenylamino)-but-2-enoic acid tert-butylester (251.3 mg, 1.0 mmol, 1.0 equiv.) was stirred with Cu(OAc)2 (544.9 mg, 3.0 mmol, 3.0 equiv.) into propionitrile (3.0 ml, 41.9 mmol, 41.9 equiv.) for 24 hours at 120° C. The dark-brown/blue raw product (295.9 mg) was analyzed by means of 1H and 19F-NMR-spectroscopy. The 19F-NMR spectra showed the desired product (δ=−112.7 ppm) and N-(4-fluorophenyl)-acetamide (δ=−118.0 ppm) in a ratio of 89:11. After purification by means of column chromatography (silica gel (50 g), pentane/EtOAc 98:2→70:30→0:100), the product was obtained in the form of a yellowish oil (222.9 mg, 0.73 mmol, 73%).
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