Water → HCID 22504378, compound

HRID 1814116Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([C:11]#[C:12][Si](C)(C)C)=[CH:9][CH:10]=1)=[O:5])[CH3:2].C1(S([NH:26][C:27]2[C:32](I)=[CH:31][C:30]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:29][CH:28]=2)(=O)=O)C=CC=CC=1.C([O-])(=O)C.[K+].O>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([C:11]2[NH:26][C:27]3[C:28]([CH:12]=2)=[CH:29][C:30]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:31][CH:32]=3)=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of the compound obtained in Example 29 (2) (0.1 g) in N,N-dimethylformamide (1 ml), 2-benzenesulfonylamino-3-iodo-5-methanesulfonylbenzene (0.0925 g), bistriphenylphosphine palladium dichloride (0.015 g), cuprous iodide (0.004 g) and potassium acetate (0.04 g) were added successively and the mixture was stirred in a sealed tube at 100° C. for 2 hours. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, washed with a saturated aqueous NaCl solution, 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 0.0462 g of the desired product as a brown solid.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washwashed with a saturated aqueous NaCl solution
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue was separated

Sources & evidence

ORD record: ord-ddd3e2552b0e4a2f8a60e6edbd4595ef
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875770B2

Reaction notes

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