Water → 1-Benzenesulfonyl-5-methanesulfonyl-2-([1,3,4]oxadiazol-2-yl)indole

HRID 1838320Notes

Reaction equation

HRID 1838320 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15](SC)=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:21]2[O:22][CH:23]=[N:24][N:25]=2)(=O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[O:27][S:28]([O-:30])=O.[K+].[OH2:32].O1CCC[CH2:34]1>>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([S:28]([CH3:34])(=[O:30])=[O:27])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:21]2[O:22][CH:23]=[N:24][N:25]=2)(=[O:8])=[O:32])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 225044011-benzenesulfonyl-5-methylthio-2-([1,3,4]oxadiazol-2-yl)-1H-indoleHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 225044261-Benzenesulfonyl-5-methanesulfonyl-2-([1,3,4]oxadiazol-2-yl)indole

Conditions

Temperature
0 °C

Procedure

To a solution of the compound obtained in Example 4 (1) (265 mg) in tetrahydrofuran (7 ml), an aqueous solution (3.5 ml) of OXONE (registered trademark) (970 mg) was added dropwise and the mixture was stirred at 0° C. for 4 hours. To the reaction solution was added water, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 262 mg of the desired product.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was separated

Sources & evidence

ORD record
ord-d186825965854cc2a9c64aac93b02cbf
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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