Potassium Iodide → HCID 57803033, compound

HRID 2102671Notes

Reaction equation

HRID 2102671 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[CH2:19]([C:6]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:8][C:7]1=[O:11])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 57803041HCID 57803041, compound

Product 1

HCID 57803033HCID 57803033, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of rac-6-chloro-3-(4-chloro-phenyl)-1,3-dihydro-indol-2-one (0.17 g, 0.6 mmol) (from Example 7b supra), benzyl bromide (0.12 g, 0.7 mmol) (Aldrich), potassium iodide (0.12 g, 0.71 mmol) and potassium carbonate (0.18 g, 1.3 mmol) in acetone (5 mL) was heated at 60° C. for 5 hours in a capped pressure tube. Mixture was then stirred at room temperature over night and then diluted with ethyl acetate (50 mL) and extracted with water (2×50 mL) and brine (50 mL). Aqueous layers were back washed with ethyl acetate (50 mL). Organic layers were combined, dried (MgSO4), filtered and concentrated. Residue was purified by flash chromatography (Biotage 40S, dichloromethane, then 5% ethyl acetate in dichloromethane as solvent) to give two products. Lower Rf sample was recrystallized from ethyl acetate-hexanes to give rac-3-benzyl-6-chloro-3-(4-chloro-phenyl)-1,3-dihydro-indol-2-one as white plates. (Yield 0.16 g, 72.4%).

Workup

  1. extractionextracted with water (2×50 mL) and brine (50 mL)
  2. washAqueous layers were back washed with ethyl acetate (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customResidue was purified by flash chromatography (Biotage 40S, dichloromethane
  7. custom5% ethyl acetate in dichloromethane as solvent) to give two products
  8. customLower Rf sample was recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-a12ed87d319b466b8ac6a2fad404235e
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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