Cl[N:2]1[C:6](=O)[CH2:5][CH2:4]C1=O.[F:9][C:10]1[C:18]([I:19])=[CH:17][CH:16]=[CH:15][C:11]=1[CH:12]=[N:13][OH:14].O.C1(N)CC1>CN(C=O)C>[CH:6]1([NH:2][C:12](=[N:13][OH:14])[C:11]2[CH:15]=[CH:16][CH:17]=[C:18]([I:19])[C:10]=2[F:9])[CH2:4][CH2:5]1N-chlorosuccinimide (1.20 g, 8.9 mmol) was added portionwise to a stirred solution of 2-fluoro-3-iodobenzaldehyde oxime (preparation 22e, 2.15 g, 8.1 mmol) in N,N′-dimethylformamide (3 mL) and the mixture was stirred for 15 minutes at 55° C. After cooling to ambient temperature, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was taken up in tetrahydrofuran (10 mL), cooled by means of an ice-water bath and cyclopropylamine (2.90 mL, 41.9 mmol) was added dropwise. After stirring 3 hours at room temperature, water was added to the reaction and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated to give the title compound (2.53 g, 96%) as a white solid.
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