[F:1][C:2]([F:18])([F:17])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[C:5]([C:12]2[O:16][CH:15]=[N:14][CH:13]=2)[CH:4]=1.[H-].[Na+].[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1.[Cl-].[NH4+]>CN(C=O)C>[CH:21]1([C:24]([N:9]2[C:10]3[C:6](=[C:5]([C:12]4[O:16][CH:15]=[N:14][CH:13]=4)[CH:4]=[C:3]([C:2]([F:17])([F:1])[F:18])[CH:11]=3)[CH:7]=[CH:8]2)=[O:25])[CH2:23][CH2:22]1To a solution of 5-(6-(trifluoromethyl)-1H-indol-4-yl)oxazole (50.0 mg) in DMF (1 mL) was added 60% sodium hydride (9.52 mg) at 0° C., and the mixture was stirred for 20 min. To the reaction mixture was added cyclopropanecarbonyl chloride (22 μL) at 0° C., and the mixture was stirred for 3 hr, saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (30.0 mg).
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