Sodium hydride → HCID 67087949, compound

HRID 570589Notes

Reaction equation

HRID 570589 reaction equation
[H-].[Na+].[NH2:3][C:4]1([C:15]2[C:16]([O:21][CH2:22][CH3:23])=[N:17][CH:18]=[CH:19][CH:20]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[NH:6][C:5]1=[O:14].[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1[S:34](Cl)(=[O:36])=[O:35]>CN(C)C=O>[NH2:3][C:4]1([C:15]2[C:16]([O:21][CH2:22][CH3:23])=[N:17][CH:18]=[CH:19][CH:20]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[N:6]([S:34]([C:27]2[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:26]=2[O:25][CH3:24])(=[O:36])=[O:35])[C:5]1=[O:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 67087991HCID 67087991, compound

Product 1

HCID 67087949HCID 67087949, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3.2 g (79 mmol) of sodium hydride (60% dispersion in mineral oil) were added in portions to a solution of 20 g (66 mmol) of 3-amino-5-chloro-3-(2-ethoxypyridin-3-yl)-1,3-dihydroindol-2-one in 50 ml of anhydrous dimethylformamide under a nitrogen atmosphere and while cooling in an ice bath. The mixture was stirred at 0° C. for 10 min and then 18.7 g (79 mmol) of 2,4-dimethoxybenzenesulfonyl chloride were added, and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into ice-water and then extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate, and the solvent was evaporated. The residue was purified by chromatography on silica gel (120 g Redisep cartridge, mobile phase gradient from 2 to 25% dichloromethane in ethyl acetate). 34 g of the title compound were obtained as a white solid.

Workup

  1. temperaturewhile cooling in an ice bath
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by chromatography on silica gel (120 g Redisep cartridge, mobile phase gradient from 2 to 25% dichloromethane in ethyl acetate)

Sources & evidence

ORD record
ord-cfbf35fcd0164b2daa14763f8ce1abc1
Source dataset
uspto-grants-2015_05
Patent number
US09023854B2

Reaction notes

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