1,4-Dioxane → HCID 57479120, compound

HRID 556486Notes

Reaction equation

HRID 556486 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.Br[C:14]1([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[NH:16][C:15]1=[O:24].O1CCOCC1>C([O-])([O-])=O.[K+].[K+]>[Cl:23][C:19]1[CH:18]=[C:17]2[C:22]([C:14]([N:8]([CH2:9][C:10]([OH:12])=[O:11])[C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[C:15](=[O:24])[NH:16]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 37803192-[(3-chlorophenyl)amino]acetic AcidHCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Product 1

HCID 57479120HCID 57479120, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

At room temperature, (3-Chloro-phenylamino)-acetic acid (1.25 g, 6.8 mmol) was dissolved in 10 ml 1N K2CO3 aqueous solution, then 3-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (2.5 g, 6.8 mmol) and 10 ml 1,4-dioxane were added slowly. After stirred for about 3 h, the solution was concentrated and the water layer was extracted with CH2Cl2. The organic layer was dried, concentrated to obtain the crude product and the crude product was purified by chromatography to obtain 1.2 g yellow solid rac-[[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-(3-chloro-phenyl)-amino]-acetic acid.

Workup

  1. concentrationthe solution was concentrated
  2. extractionthe water layer was extracted with CH2Cl2
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto obtain the crude product
  6. customthe crude product was purified by chromatography

Sources & evidence

ORD record
ord-754096abfd684783b832a8269d148724
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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