Sodium Carbonate → HCID 57803077, compound

HRID 2102667Notes

Reaction equation

HRID 2102667 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](O)([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[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][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 57803086HCID 57803086, compound

Product 1

HCID 57803077HCID 57803077, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Crude rac-6-chloro-3-hydroxy-3-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one (from Example 6a 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 recrystallized from dichloromethane-hexanes to give rac-6-chloro-3-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one as off-white prisms. (Yield 2.12 g, 77.4% 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 recrystallized from dichloromethane-hexanes

Sources & evidence

ORD record
ord-2e07d31ba72e4fa69bbf65793a5b4d8d
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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