Trifluoroacetic acid → HCID 57803087, compound

HRID 2102724Notes

Reaction equation

HRID 2102724 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH3:20])[CH:14]=3)(O)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH3:20])[CH:14]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 57803071HCID 57803071, compound

Product 1

HCID 57803087HCID 57803087, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Crude rac-6-chloro-3-(3,4-dimethyl-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one (0.25 g, 0.87 mmol) (from Example 52a supra) was suspended in a mixture of triethylsilane (0.41 mL, 2.61 mmol) (Aldrich) and trifluoroacetic acid (1.48 g, 13.1 mmol) and heated in an 80° C. oil bath for 17 hours. After cooling to room temperature, mixture was diluted with ethyl acetate and treated with solid sodium carbonate (1 g). After stirring for 30 minutes, mixture was extracted with water and brine. Aqueous layers were back washed with ethyl acetate. Organic layers were combined, dried (Na2SO4), filtered and concentrated. Residue was recrystallized from dichloromethane-hexanes to give rac-6-chloro-3-(3,4-dimethyl-phenyl)-1,3-dihydro-indol-2-one as a brown solid. (Yield 0.18 g, 78%)

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionmixture was extracted with water and brine
  3. washAqueous layers were back washed with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customResidue was recrystallized from dichloromethane-hexanes

Sources & evidence

ORD record
ord-984eb4cb60dd456ca7522da42b186090
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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