Sodium Hydroxide → 2-(6-chloro-5-fluoro-1H-indol-2-yl)-1-ethylsulfanyl-propan-2-ol

Temperatur

50 °C

To a solution of 2-(6-chloro-5-fluoro-1-methanesulfonyl-1H-indol-2-yl)-1-ethylsulfanyl-propan-2-ol (0.30 g, 0.82 mmol) in methanol (10 mL) was added 4M sodium hydroxide solution (0.4 mL). The reaction was allowed to proceed overnight at room temperature. Complete reaction was not achieved, so additional 1M sodium hydroxide solution (1 mL) was added and the reaction mixture was heated to 50° C. The reaction mixture was kept at 50° C. for two hours then allowed to stir overnight at room temperature. The reaction mixture was concentrated and to the concentrate was added 1N hydrochloric acid solution and water. The mixture was extracted twice with ethyl ether. The extracts were dried over Mg2SO4, filtered, and evaporated to yield a residue. The residue was purified by column chromatography eluting with dichloromethane to yield the title compound as a yellow oil.

1. customComplete reaction
2. waitThe reaction mixture was kept at 50° C. for two hours
3. concentrationThe reaction mixture was concentrated and to the concentrate
4. additionwas added 1N hydrochloric acid solution and water
5. extractionThe mixture was extracted twice with ethyl ether
6. dry with materialThe extracts were dried over Mg2SO4
7. filtrationfiltered
8. customevaporated
9. customto yield a residue
10. customThe residue was purified by column chromatography
11. washeluting with dichloromethane

ORD-Eintrag

ord-ad53b4b302eb4f62a16a78720f051fb3

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09434688B2