Water → 6-(1-Benzenesulfonyl-5-methylthio-1h-pyrrolo[2,3-b]pyridin-2-yl)nicotinic acid ethyl ester

HRID 1814113Notes

Reaction equation

[C:1]1([S:7]([NH:10][C:11]2[C:16](I)=[CH:15][C:14]([S:18][CH3:19])=[CH:13][N:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([O:22][C:23]([C:25]1[CH:26]=[CH:27][C:28]([C:31]#[C:32][Si](C)(C)C)=[N:29][CH:30]=1)=[O:24])[CH3:21].C([O-])(=O)C.[K+].O>O1CCOCC1>[CH2:20]([O:22][C:23](=[O:24])[C:25]1[CH:26]=[CH:27][C:28]([C:31]2[N:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[C:11]3=[N:12][CH:13]=[C:14]([S:18][CH3:19])[CH:15]=[C:16]3[CH:32]=2)=[N:29][CH:30]=1)[CH3:21]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-benzenesulfonylamino-5-methylthio-3-iodo-pyridine (100 mg) in 1,4-dioxane (2.5 ml), 5-ethoxycarbonyl-2-trimethylsilylethynylpyridine (185 mg), bistriphenylphosphine palladium dichloride (9 mg), cuprous iodide (5 mg) and potassium acetate (37 mg) were added successively and the mixture was stirred in a sealed tube at 100° C. for 15 hours. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, 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=2:1) to obtain 110 mg of the desired product as an orange oil.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue was separated

Sources & evidence

ORD record: ord-0f1fd7e7c0f54fbc91234c3ff00dc5b1
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875770B2

Reaction notes

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