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

Temperature

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 record

ord-6b8a4018df524261bf565b31da94ef4d

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394971B2