Potassium Iodide → HCID 11998661, compound

HRID 2102728Notes

Reaction equation

HRID 2102728 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]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]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]([CH2:25][C:24]3[CH:27]=[CH:28][CH:29]=[C:22]([Cl:21])[CH:23]=3)([C:12]3[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 57803030HCID 57803030, compound

Product 1

HCID 11998661HCID 11998661, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of rac-6-chloro-3-(4-isopropyl-phenyl)-1,3-dihydro-indol-2-one (0.11 g, 0.38 mmol) (from Example 53b supra), 3-chlorobenzyl bromide (0.093 g, 0.454 mmol) (Aldrich), potassium iodide (0.0762 g, 0.44 mmol) and potassium carbonate (0.114 g, 0.82 mmol) in acetone (3 mL) was heated at 70° C. for 3 hours. After cooling, mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate three times. 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-(4-isopropyl-phenyl)-1,3-dihydro-indol-2-one as brown solid. (Yield 0.09 g, 56.9%).

Workup

  1. temperatureAfter cooling
  2. custommixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate three times
  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-5b7e2f56123444b8a2db141a1437cdc0
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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