Ammonium Chloride → 7-chloro-5-fluoro-4-methyl-1H-indole

Temperatur

-50 °C

Under an atmosphere of argon, 4-chloro-2-fluoro-5-nitrotoluene (1.9 g) was dissolved with anhydrous tetrahydrofuran (100 mL), and the reaction mixture was stirred at −50° C. Vinylmagnesium bromide (1.0 M solution in tetrahydrofuran, 40 mL) was dropped to the reaction mixture. The reaction mixture was raised slowly to −20° C. for 40 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and a saturated salt solution. The obtained extract was concentrated under reduced pressure after drying with sodium sulfate. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=95:5→91:9) to give the title compound (1.09 g) having the following physical data.

1. temperatureThe reaction mixture was raised slowly to −20° C. for 40 minutes
2. extractionthe reaction mixture was extracted with ethyl acetate
3. washThe obtained organic layer was washed with water
4. extractionThe obtained extract
5. concentrationwas concentrated under reduced pressure
6. dry with materialafter drying with sodium sulfate
7. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=95:5→91:9)

ORD-Eintrag

ord-84723478833a4dc8beee4f4e0a253693

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08569504B2