[F:1][C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:3]=1[NH:4][C:5](=[O:10])[C:6]([F:9])([F:8])[F:7].CI.[C:20]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:3]=1[N:4]([CH3:20])[C:5](=[O:10])[C:6]([F:7])([F:8])[F:9]To a solution of compound 32-NO2—H (13.9 g, 55.2 mmol) and MeI (14.8 g, 0.104 mol) in DMF (80 mL), K2CO3 (12.5 g, 90.6 mmol) was added. After vigorous stirring for 24 h at 90° C., volatile materials were evaporated in vacuum. The residue was diluted with water (200 mL), the organic layer was separated, and the aqueous layer was extracted with ether (3×100 mL). Combined organic solutions were dried, and the solvent was evaporated at an ambient pressure (bath temperature 50° C.). The title compound was isolated by chromatography on SiO2 (600 g) with hexane/EtOAc mixture (1:0→1:1) as an eluent; yellowish oil (13.6 g, purity ca. 90%, yield 83%). 1H NMR (CDCl3, 300 MHz, ppm): δ=3.36 (s, 3 H, CH3), 7.39 (t, 3JHH=JHF=8.8, 1H, H-3), 8.25 (dd, 4JHH=2.6, 4JHF=6.5, 1H, H-6), 8.32-8.38 (m, 1H, H-4); EI-MS: m/z (rel. int., %)=266 (100) [M], 197 (57) [M-CF3], 184 (32), 170 (23), 123 (37), 110 (18).
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