Sodium Carbonate → HCID 57803080, compound

HRID 2102661Notes

Reaction equation

HRID 2102661 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](O)([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 57803078HCID 57803078, compound

Product 1

HCID 57803080HCID 57803080, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

rac-6-Chloro-3-hydroxy-3-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one (from Example 4a supra) was suspended in a mixture of triethylsilane (5 mL, 31.3 mmol) (Aldrich) and trifluoroacetic acid (12.5 mL) and heated in an 90° C. oil bath for 17 hours. After cooling to room temperature, mixture was diluted with ethyl acetate (100 mL) and treated with solid sodium carbonate (10.5 g). After stirring for 30 minutes, mixture was extracted with water (2×100 mL) and brine (100 mL). Aqueous layers were back washed with ethyl acetate (100 mL). Organic layers were combined, dried (MgSO4), filtered and concentrated. Residue was purified by flash chromatography (Biotage 40M, dichloromethane then 10% ethyl acetate in dichloromethane as solvent). Fractions containing product were combined, concentrated and recrystallized from dichloromethane-hexanes to give rac-6-chloro-3-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one as white needles. (Yield 2.26 g, 82.6% over two steps).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionmixture was extracted with water (2×100 mL) and brine (100 mL)
  3. washAqueous layers were back washed with ethyl acetate (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customResidue was purified by flash chromatography (Biotage 40M, dichloromethane
  8. additionFractions containing product
  9. concentrationconcentrated
  10. customrecrystallized from dichloromethane-hexanes

Sources & evidence

ORD record
ord-45bf1af111b745078c01413d8a844917
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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