Ethyl Acetate → n-[3-Tert-butyl-1-(4,4,4-trifluorobutyl)-1h-pyrazol-5-yl]-2-fluoro-5-(trifluoromethyl)benzamide

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Reaction Steps

To a solution of Example 135B (2.0 g, 8.1 mmol) and Et3N (3.4 mL, 24.3 mmol) in THF (40 mL) was added 2-fluoro-5-(trifluoromethyl)benzoyl chloride (1.2 mL, 8.1 mmol). The mixture was allowed to stir at ambient temperature for 3 h then partitioned between saturated aqueous NaHCO3 (10 mL) and EtOAc (10 mL). The layers were separated and the aqueous phase was extracted EtOAc (3×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification by column chromatography (SiO2, 50% hexanes/EtOAc then 100% EtOAc then 9:1:0.1 EtOAc:MeOH:Et3N) afforded the title compound (2.9 g, 6.5 mmol, 80% yield). MS (ESI+) m/z 440 (M+H)+.

Provenance & Evidence