[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH:16]1([N:19]2[C:27]3[C:22](=[C:23](O)[CH:24]=[C:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:26]=3)[CH:21]=[CH:20]2)[CH2:18][CH2:17]1.N1C=CC=CC=1.Cl>C(Cl)(Cl)Cl>[CH:16]1([N:19]2[C:27]3[C:22](=[C:23]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:24]=[C:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:26]=3)[CH:21]=[CH:20]2)[CH2:17][CH2:18]1In a 500-mL egg plant-type flask, a chloroform (50 mL) solution of trifluoromethanesulfonic acid anhydride (6.30 mL, 37.5 mmol) was dropwise added to a chloroform (100 mL) solution of ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate (6.12 g, 25 mmol) and pyridine (6.06 mL, 75 mmol) with cooling with ice, and stirred at that temperature for 30 minutes, then poured into aqueous hydrochloric acid solution, extracted with chloroform, washed with aqueous saturated sodium hydrogencarbonate solution, and dried with sodium sulfate. The reaction solution was filtered, concentrated, and purified through silica gel column chromatography (Biotage [SiO2, 40+M]) with a hexane/ethyl acetate developer system to obtain the title compound as a colorless oil.
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