Water → 2-(5-chloro-6-(trifluoromethyl)-1H-indol-2-yl)-1-(4-fluorophenylsulfonyl)propan-2-ol

HRID 1945147Notes

Reaction equation

HRID 1945147 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[NH:7][C:6]([C:15]([OH:26])([CH3:25])[CH2:16][S:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[CH:5]2.[OH:27]OS([O-])=O.[K+].[OH2:33]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([F:12])([F:13])[F:14])[NH:7][C:6]([C:15]([OH:26])([CH3:25])[CH2:16][S:17]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)(=[O:27])=[O:33])=[CH:5]2

Participants

6

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 444191882-(5-chloro-6-(trifluoromethyl)-1H-indol-2-yl)-1-(4-fluorophenylthio)propan-2-ol

Product 1

HCID 116978032-(5-chloro-6-(trifluoromethyl)-1H-indol-2-yl)-1-(4-fluorophenylsulfonyl)propan-2-ol

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(5-chloro-6-trifluoromethyl-1H-indol-2-yl)-1-(4-fluoro-phenylsulfanyl)-propan-2-ol (0.42 g, 1.04 mmol) in dichloromethane (10 mL) was added water (10 mL). The solution was stirred rapidly and tetrabutylammonium hydrogensulfate (12 mg, 0.035 mmol) was added followed by OXONE® (1.02 g, 1.66 mmol). The reaction mixture turned bright yellow and was allowed to proceed overnight at room temperature. The reaction mixture was diluted with water and dichloromethane, the layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, twice with 10% sodium thiosulfate solution and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated and pre-absorbed onto silica gel and purified by column chromatography eluting with 80% diethyl ether/pentane to yield the title product as a solid.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with water, twice with 10% sodium thiosulfate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. concentrationthe filtrate was concentrated
  7. custompre-absorbed onto silica gel
  8. custompurified by column chromatography
  9. washeluting with 80% diethyl ether/pentane

Sources & evidence

ORD record
ord-30a5e3c5e6b945b096b787cc90f983db
Source dataset
uspto-grants-2013_03
Patent number
US08394971B2

Reaction notes

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