Potassium Iodide → HCID 11998534, compound

HRID 2102718Notes

Reaction equation

HRID 2102718 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[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:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[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 57803073HCID 57803073, compound

Product 1

HCID 11998534HCID 11998534, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of rac-6-chloro-3-naphthalen-2-yl-1,3-dihydro-indol-2-one (0.07 g, 0.24 mmol) (from Example 47b supra), 3-chlorobenzyl bromide (0.053 g, 0.28 mmol) (Aldrich), potassium iodide (0.047 g, 0.28 mmol) and potassium carbonate (0.071 g, 0.52 mmol) in acetone (3 mL) was heated at 65° C. for 2 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-naphthalen-2-yl-1,3-dihydro-indol-2-one as a brown solid. (Yield 0.02 g, 20.2%).

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-34e3b68d0a0d45d9be35944a60d2a7bc
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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