Dimethylformamide → 6-chloro-5-(trifluoromethyl)-1H-indole

A mixture of 5-chloro-4-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline (16.5 g), copper(I) iodide (20.4 g) and dimethylformamide (100 ml) was stirred at room temperature for 10 min and then stirred with heating at 100° C. for 2.5 hr. The reaction mixture was allowed to cool, diethyl ether was added and the mixture was stirred at room temperature. The reaction mixture was filtered through a celite (trademark) filter, and the filtrate was washed with water and saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a brown oil. The oil was purified by silica gel column chromatography (elution solvent:ethyl acetate-hexane (1:5-1:3)) to give 6-chloro-5-(trifluoromethyl)-1H-indole (5.75 g, yield 46%).

1. stirringstirred
2. temperaturewith heating at 100° C. for 2.5 hr
3. temperatureto cool
4. stirringthe mixture was stirred at room temperature
5. filtrationThe reaction mixture was filtered through a celite (trademark)
6. filtrationfilter
7. washthe filtrate was washed with water and saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. customThe solvent was evaporated under reduced pressure
10. customto give a brown oil
11. customThe oil was purified by silica gel column chromatography (elution solvent:ethyl acetate-hexane (1:5-1:3))

ORD record

ord-2dbd9636e5ca4c3aa8ca4ca2bf838207

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994196B2