Methanol → 5-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-hydroxy-3-(2-ethoxyphenyl)-indol-2-one

HRID 1091547Notes

Reaction equation

HRID 1091547 reaction equation
C([O-])(C)(C)C.[K+].[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[C:12]2([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH2:27][CH3:28])[OH:19])#[N:8].[CH3:29][O:30][C:31]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:32]=1[S:39](Cl)(=[O:41])=[O:40].CO>CN(C)C=O>[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:39]([C:32]1[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:31]=1[O:30][CH3:29])(=[O:41])=[O:40])[C:13](=[O:18])[C:12]2([OH:19])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH2:27][CH3:28])#[N:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 665930415-Cyano-3-(2-ethoxyphenyl)-3-hydroxy-indol-2-one

Product 1

HCID 665929935-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-hydroxy-3-(2-ethoxyphenyl)-indol-2-oneYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.7 g (15 mmol) of potassium tert-butanolate were added in portions to 4 g (13.6 mmol) of the intermediate 1b in 40 ml of anhydrous dimethylformamide at 0° C., and the mixture was stirred for about 90 minutes. Then 3.4 g (14.3 mmol) of 2,4-dimethoxybenzenesulfonyl chloride were rapidly added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 2 h. This solution was then poured into an ice-water/K2CO3 solution, resulting in a precipitate which was isolated. The resulting residue was treated with a little methanol, filtered off with suction and dried, resulting in 3.3 g of the product.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 2 h
  2. customresulting in a precipitate which
  3. customwas isolated
  4. filtrationfiltered off with suction
  5. customdried

Sources & evidence

ORD record
ord-abffd40b5f6044ca92618cb63502bc76
Source dataset
uspto-grants-2012_03
Patent number
US08129389B2

Reaction notes

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