Water → HCID 67196875, compound

HRID 469197Notes

Reaction equation

HRID 469197 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[C:11]([C:12]2([OH:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([I:21])[CH:19]=3)[NH:14][C:13]2=[O:22])=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:4].[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].O>CN(C=O)C.C(OCC)C>[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1[S:34]([N:14]1[C:15]2[C:20](=[CH:19][C:18]([I:21])=[CH:17][CH:16]=2)[C:12]([C:11]2[C:6]([O:5][CH2:3][CH3:4])=[N:7][CH:8]=[CH:9][CH:10]=2)([OH:23])[C:13]1=[O:22])(=[O:35])=[O:36]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 67049044HCID 67049044, compound

Product 1

HCID 67196875HCID 67196875, compoundYield 255%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (145 mg of a 50% strength dispersion in mineral oil, 3.03 mmol) was added to an ice-cooled solution of 3-(2-ethoxypyridin-3-yl)-3-hydroxy-5-iodo-1,3-dihydroindol-2-one (1.0 g, 2.52 mmol) in DMF (20 ml). The reaction mixture was stirred at 0° C. for 15 minutes and then 2,4-dimethoxyphenylsulfonyl chloride (99 mg, 0.48 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours, water was added, and the resulting precipitate was filtered off. The precipitate formed after stirring in ethyl ether (50 ml) overnight was filtered off with suction, resulting in 730 mg of the title compound (45% yield).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. filtrationthe resulting precipitate was filtered off
  3. customThe precipitate formed
  4. filtrationwas filtered off with suction

Sources & evidence

ORD record
ord-1f080d10ca2f45c1bb21e63f68d019cc
Source dataset
uspto-grants-2014_01
Patent number
US08629148B2

Reaction notes

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