Water → 2-(2-Tetrahydrofuranyl)-5-methanesulfonyl-1-benzenesulfonylindole

HRID 1838340Notes

Reaction equation

[C:1]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:12]=2I)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([CH:24]1[CH2:28][CH2:27][CH2:26][O:25]1)#[CH:23].C(N(CC)CC)C.O>O1CCOCC1>[O:25]1[CH2:26][CH2:27][CH2:28][CH:24]1[C:22]1[N:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[C:11]2[C:12]([CH:23]=1)=[CH:13][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][CH:16]=2

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-benzenesulfonylamino-2-iodo-4-methanesulfonylbenzene (256 mg) in 1,4-dioxane (6 ml), 2-ethynyltetrahydrofuran (169 mg), bistriphenylphosphine palladium dichloride (21 mg), cuprous iodide (11 mg) and triethylamine (89 mg) were added successively and the mixture was stirred in a sealed tube at 60° C. for 3 hours. After cooling, the reaction solution was 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 218 mg of the desired product in a white amorphous form.

Workup

temperatureAfter cooling
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-69ea4f2f131c4410be81dd751da3a87c
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673797B1

Reaction notes

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