Water → Indole

Participants

Reaction Steps

In a 50 ml reaction vessel, to a solution of 4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indole (100 mg) in DMF (1 ml) was added 60% NaH (10.9 mg) at 0° C. The solution was warmed to room temperature, followed by stirring for 0.5 hour. Further, tertiary-butyl (2-iodoethoxy)dimethylsilane was added thereto at 0° C., followed by stirring at room temperature for 15 hours. Completion of the reaction was confirmed by LC-MS, and then the reaction solution was added with water (30 ml). It was extracted three times with EtOAc (20 ml). The organic layer was washed with saturated brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. It was purified by silica gel column chromatography (automatic purifier, n-hexane:EtOAc=100:0 to 90:10) to obtain 1-(2-{[tertiary-butyl(dimethyl)silyl]oxy}ethyl)-4-{5-[3-(trifluoromethyl)-4-2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indole (86.4 mg) as a white solid.

Provenance & Evidence