[C:1]([CH2:3][C:4]([O:6]CC)=O)#[N:2].[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19](=[O:23])/[CH:20]=[CH:21]/[CH3:22])=[CH:12][CH:11]=1.CC(C)([O-])C.[K+].O1CCCC1>C(O)(C)(C)C.Cl>[F:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][N:18]2[C:19](=[O:23])[CH2:20][C@@H:21]([CH3:22])[C@H:3]([C:1]#[N:2])[C:4]2=[O:6])=[CH:14][CH:15]=1A solution of ethyl cyanoacetate (4.26 mL, 40 mmol) and trans-2-butenoic acid [2-(4-fluoro-phenyl)ethyl]amide (4.15 g, 20 mmol) in tert-butanol (60 mL) was treated with a solution of potassium tert-butoxide in tetrahydrofuran (1.0 M, 40 mL, 40 mmol) and the mixture was heated at 80° C. The mixture was cooled to room temperature after 16.5 hours and diluted with 1.0 N aqueous hydrochloric acid. The mixture was concentrated under vacuum to remove the organic solvents, providing a suspension of solid in the aqueous residue. This was collected by filtration, dried, and purified by recrystallization from 95% ethanol to provide a white solid (5.13 g, 93%). 1H NMR (300 MHz, CDCl3) δ7.19 (m, 2H), 7.00 (t, J=9 Hz, 2H), 4.02 (m, 2H), 3.41 (d, J=11 Hz, 1H), 2.91 (m, 1H), 2.83 (t, J=8 Hz, 2H), 2.5-2.3 (m, 2H), 1.31 (d, J=6 Hz, 3H). Mass spec (CI) m/z 275.0 (M+H+, 100%).
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