Trifluoroacetic acid → HCID 57803049, compound

HRID 2102654Notes

Reaction equation

HRID 2102654 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2(O)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 225609075-Chloro-3-hydroxy-3-(4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 57803049HCID 57803049, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of rac-5-chloro-3-hydroxy-3-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one (1.0 g, 3.45 mmol) (from Example 1a supra) in a mixture of triethylsilane (2 mL, 12.5 mmol) (Aldrich) and trifluoroacetic acid (5 mL, 65 mmol) was heated at 100° C. for 24 hours. After cooling, mixture was diluted with toluene and concentrated to almost dryness. Residue was dissolved in dichloromethane and purified by flash chromatography (Biotage 40M, 5% then 10% ethyl acetate in dichloromethane as solvent). Fractions containing product were combined and concentrated. Residue was recrystallized from dichloromethane-hexanes in two crops to give rac-5-chloro-3-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one as white needles. (Yield 0.60 g, 63.5%).

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrated to almost dryness
  3. dissolutionResidue was dissolved in dichloromethane
  4. custompurified by flash chromatography (Biotage 40M, 5%
  5. additionFractions containing product
  6. concentrationconcentrated
  7. customResidue was recrystallized from dichloromethane-hexanes in two crops

Sources & evidence

ORD record
ord-da35d6bbb2914192815492c0517b46d9
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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