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

HRID 1814057Notes

Reaction equation

HRID 1814057 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-416e6fa718a244368cbef60fff4f72a2
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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