[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[H-].[Na+].[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17](F)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1.Cl>CN(C=O)C.C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([CH:5]([C:6]#[N:7])[C:4]([O:3][CH2:1][CH3:2])=[O:8])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1
Ethylcyanoacetate (1.14 g, 10.0 mmol, 2 eq) in 1 mL DMF was added at 0° C. to a suspension of sodium hydride (0.4 g, 60% in mineral oil, 5.02 mmol) in 3 mL DMF under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 30 minutes before the dropwise addition of 4-fluoro-3-nitro-benzoic acid methyl ester (1.05 g, 22.7 mmol) in 5 mL DMF. After stirring for 2 hours at room temperature, 2 M HCl (20 mL) and ethyl acetate (20 mL) were added to the red solution. The organic layer was washed with water and brine, dried over sodium sulphate and concentrated to give the title compound as an orange oil, which was used without further purification (1.47 g, 5.03 mmol). 1H NMR (CDCl3) δ 8.83 (1H, d, J=1.5), 8.38 (1H, dd, J=8.0, 1.8), 7.89 (1H, d, J=8.1), 5.74 (1H, s), 4.30 (2H, q, J=7.1), 4.00 (3H, s), 1.32 (3H, t, J=7.0).
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