Pyridine → 3-amino-4-bromo-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

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Reaction Steps

To a solution of 2,6-dichloro-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (1.02 g, 3.1 mmol) (Example 6.3) in anhydrous dichloromethane (25 ml), at 20° C., was added sequentially pyridine (0.74 g, 2.0 mmol) and 4-bromo-3-sulfinylamino-benzoyl chloride (0.94 g, 9.30 mmol) (Example 1.2). The reaction mixture was stirred at ambient temperature for one hour. The reaction mixture was then heated to 50° C. for 16 hours. The reaction mixture was allowed to cool to ambient temperature before adding dimethylformamide (50 ml). The dichloromethane was distilled off and the reaction mixture was heated to 130° C. for 16 hours. The reaction was quenched by addition of aqueous sodium hydrogen carbonate (saturated) (10 ml). After separation of the phases, the aqueous layer was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:5 to 1:0) to give 3-amino-4-bromo-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (quantitative, 100% yield). 1H-NMR (CDCl3, 400 MHz): 7.73 (m, 3H), 7.27 (m, 3H), 6.91 (m, 1H), 3.9 (s, 2H) ppm.

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