Trifluoroacetic acid → HCID 57803064, compound

HRID 2102658Notes

Reaction equation

HRID 2102658 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]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-].[K+].[K+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 57803059HCID 57803059, compound

Product 1

HCID 57803064HCID 57803064, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of rac-6-chloro-3-cyclopentyl-3-hydroxy-1,3-dihydro-indol-2-one (1.0 g, 4 mmol) (from Example 3a, supra) in a mixture of triethylsilane (2 mL, 12.5 mmol) (Aldrich) and trifluoroacetic acid (5 mL, 65 mmol) was heated in a 100° C. bath for 48 hours. After cooling to room temperature, mixture was diluted with ethyl acetate (50 mL). Solid potassium carbonate was added and mixture stirred at room temperature for 1 hour. Mixture was filtered and concentrated. Residue was redissolved in ethyl acetate and adsorbed onto silica gel (10 g). Solvent was evaporated off. Material was purified by flash chromatography (Biotage 40 M, 5% then 10% ethyl acetate in dichloromethane as solvent). Main product fractions were collected and concentrated to give rac-6-chloro-3-cyclopentyl-1,3-dihydro-indol-2-one as a dark purple solid. (Yield 0.24 g, 25.6%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationMixture was filtered
  3. concentrationconcentrated
  4. dissolutionResidue was redissolved in ethyl acetate
  5. customSolvent was evaporated off
  6. customMaterial was purified by flash chromatography (Biotage 40 M, 5%
  7. customMain product fractions were collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f5bdb6f2649f422cb581ba089abdb89a
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

Loading…