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Potassium Iodide → Rac-6-chloro-3-(3-chloro-benzyl)-3-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one

HRID 2102709
Notes
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Reaction equation

HRID 2102709 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[C:23]([Cl:22])[CH:24]=3)([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 57803047Rac-6-chloro-3-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one

Product 1

HCID 11998413Rac-6-chloro-3-(3-chloro-benzyl)-3-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of rac-6-chloro-3-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one (0.1 g, 0.33 mmol) (from Example 40b supra), 3-chlorobenzyl bromide (0.080 g, 0.38 mmol) (Aldrich), potassium iodide (0.065 g, 0.38 mmol) and potassium carbonate (0.098 g, 0.71 mmol) in acetone (5 mL) was heated at 60° C. for 2 hours. After cooling, mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried (Na2SO4), filtered and concentrated. Residue was purified by chromatography to give rac-6-chloro-3-(3-chloro-benzyl)-3-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one as a white solid. (Yield 0.1 g, 71.4%).

Workup

  1. temperatureAfter cooling
  2. custommixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customResidue was purified by chromatography

Sources & evidence

ORD record
ord-e3150624a5c14f498b8b44a144521a49
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576082B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes