Dimethylformamide → 1-Benzenesulfonyl-2-(5-ethoxycarbonylpyridin-2-yl)-5-methanesulfonylindole

HRID 1838349Notes

Reaction equation

HRID 1838349 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][Si](C)(C)C)=[N:10][CH:11]=1)=[O:5])[CH3:2].[C:18]1([S:24]([NH:27][C:28]2[C:33](I)=[CH:32][C:31]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:30][CH:29]=2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(=O)C.[K+].CN(C)C=O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.O>[C:18]1([S:24]([N:27]2[C:28]3[C:29](=[CH:30][C:31]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:32][CH:33]=3)[CH:13]=[C:12]2[C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][N:10]=2)(=[O:25])=[O:26])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 517044Potassium AcetateHCID 225043761-Benzenesulfonylamino-2-iodo-4-methanesulfonylbenzeneHCID 225043975-Ethoxycarbonyl-2-trimethylsilylethynylpyridine

Product 1

HCID 225044091-Benzenesulfonyl-2-(5-ethoxycarbonylpyridin-2-yl)-5-methanesulfonylindoleYield 31.5%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-ethoxycarbonyl-2-trimethylsilylethynylpyridine (3.80 g), 2-benzenesulfonylamino-3-iodo-5-methanesulfonylbenzene (3.50 g), potassium acetate (6.00 g), cuprous iodide (75 mg), dichlorobis(triphenylphosphine)palladium (0.27 g) and N,N-dimethylformamide (10 ml) was stirred under nitrogen atmosphere at 100° C. for 8 hours. To the reaction solution was then added water and ethyl acetate. The insolubles were filtered off. The filtrate was extracted with ethyl acetate and washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (methanol:dichloromethane=1:100) to obtain 1.22 g of the desired product.

Workup

  1. filtrationThe insolubles were filtered off
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washwashed with a saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7df2a42e2974b478d3bf9b281499f85
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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