Trifluoroacetic acid → Rac-6-chloro-3-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one

HRID 2102708Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[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]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Crude rac-6-chloro-3-(3,5-dimethoxy-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one (0.3 g, 0.94 mmol) (from Example 40a supra) was suspended in a mixture of triethylsilane (0.45 mL, 2.82 mmol) (Aldrich) and trifluoroacetic acid (1.38 g, 14.1 mmol) and heated in an 90° 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-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one as yellow solid. (Yield 0.2 g, 71%)

Workup

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

Sources & evidence

ORD record: ord-412eb060f4ae4f9ab85c5a1e5558430d
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576082B2

Reaction notes

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