Water → 2-(2-tetrahydrofuranyl)-5-methanesulfonyl-1H-indole

HRID 1838341Notes

Reaction equation

HRID 1838341 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[N:7](S(C2C=CC=CC=2)(=O)=O)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2.[OH-].[K+].O>O1CCCC1.CO>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 225044492-(2-Tetrahydrofuranyl)-5-methanesulfonyl-1-benzenesulfonylindole

Product 1

HCID 225044162-(2-tetrahydrofuranyl)-5-methanesulfonyl-1H-indoleYield 82.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the compound obtained in Example 13 (1) (210 mg) in a mixture of tetrahydrofuran/methanol (2:1, 15 ml), a 1N aqueous potassium hydroxide solution (1.6 ml) was added and the mixture was stirred at 100° C. for 2 hours. The reaction solution was then poured into water, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) to obtain 113 mg of the desired product as a white powder.

Workup

  1. extractionextracted with dichloromethane
  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-12c67c51385a4087ad7abe2bfac10a82
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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