[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[C:5]([F:12])[CH:4]=1)#[N:2].[CH2:13]([O:15][C:16](=[O:21])[C:17]([NH2:20])=[N:18]O)[CH3:14].O>ClCCl.CC1C=CC=C(C)N=1>[CH2:13]([O:15][C:16]([C:17]1[N:20]=[C:7]([C:6]2[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[F:12])[O:8][N:18]=1)=[O:21])[CH3:14]A solution of 4-cyano-2-fluorobenzoyl chloride (450 mg) in dichloromethane (5 mL) is added to a solution of amino-hydroxyimino-acetic acid ethyl ester (350 mg) in 2,6-dimethyl-pyridine (1 mL) and the reaction mixture is stirred at room temperature over night. Water is added and the organic phase is separated, washed with 1 N hydrochloric acid, water, and brine, dried over MgSO4, and concentrated in vacuo. The dark residue is heated to 170° C. for 2 h. The crude product is purified by silica gel chromatography (cyclohexane/ethyl acetate 65:35). LC (method 15): tR=1.08 min; Mass spectrum (ESI+): m/z=262 [M+H]+.
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