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

HRID 1432234Notes

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

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

extractionextracted with dichloromethane
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue was separated

Sources & evidence

ORD record: ord-da412c11b5ed440ea554ecfc5b6c0eb7
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612070B2

Reaction notes

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