Br[CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:3]1=[O:9].[Cl:10][C:11]1[C:12]([C:17]([F:20])([F:19])[F:18])=[N:13][NH:14][C:15]=1[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:10][C:11]1[C:12]([C:17]([F:19])([F:18])[F:20])=[N:13][N:14]([CH:2]2[CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:3]2=[O:9])[C:15]=1[CH3:16]To a solution of 3-bromooxepan-2-one (1 g, 5.18 mmol) in DMF (10 mL) was added 4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazole (0.956 g, 5.18 mmol), followed by potassium carbonate (1.07 g, 7.74 mmol). The reaction mixture was then heated at 65° C. for 8 h. After cooling to room temperature, the reaction mixture was partitioned between water (20 mL) and ethyl acetate (30 mL). The organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography (SiO2, 25% EtOAc/hexanes) gave the title product as a white solid (0.3 g, 1.01 mmol, 20%).
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