Trifluoroacetic acid → HCID 57803072, compound

HRID 2102680Notes

Reaction equation

HRID 2102680 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](O)([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)[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:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 57803054HCID 57803054, compound

Product 1

HCID 57803072HCID 57803072, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

rac-6-Chloro-3-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-1,3-dihydro-indol-2-one (0.22 g, 0.84 mmol) (from Example 14a supra) was suspended in a mixture of triethylsilane (0.40 mL, 2.52 mmol) (Aldrich) and trifluoroacetic acid (1.2 mL, 12.5 mmol) (Aldrich) and heated in an 90° C. oil bath for 17 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate (10 mL) and treated with solid sodium carbonate (1.0 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 triturated with dichloromethane-hexanes to give rac-6-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1,3-dihydro-indol-2-one as a white solid. (Yield 0.1 g, 50%).

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 triturated with dichloromethane-hexanes

Sources & evidence

ORD record
ord-9486ff1ab41840dba227419af73f0ddb
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

Loading…