[NH2:1][C:2]1[C:3]([F:34])=[C:4]([CH:29]=[CH:30][C:31]=1[C:32]#[N:33])[C:5]([NH:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][C:11]([C:18]([F:27])([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20])=[CH:10][C:9]=1[Br:28])=[O:6].[Cl:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][N:37]=1.O.C(OCC)(=O)C>CN1C(=O)N(C)CC1>[Br:28][C:9]1[CH:10]=[C:11]([C:18]([F:27])([C:19]([F:20])([F:21])[F:22])[C:23]([F:24])([F:25])[F:26])[CH:12]=[C:13]([C:14]([F:16])([F:17])[F:15])[C:8]=1[NH:7][C:5]([C:4]1[C:3]([F:34])=[C:2]([NH:1][C:40](=[O:41])[C:39]2[CH:43]=[CH:44][C:36]([Cl:35])=[N:37][CH:38]=2)[C:31]([C:32]#[N:33])=[CH:30][CH:29]=1)=[O:6]To a solution of 0.0500 g (0.0877 mol) of 3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-cyano-2-fluorobenzamide in 0.200 ml of DMI was added 0.0308 g (0.175 mmol) of 6-chloronicotinoylchloride, followed by stirring at 130° C. for 6 hours. To the reaction liquid were added water and ethyl acetate, and the organic layer was washed with 1 M hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=2:1) to prepare 0.0100 g (yield 16%) of a target compound.
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