Phenylboronic Acid → 6-Phenyl-1,3-dihydro-indol-2-one

HRID 1386347Notes

Reaction equation

HRID 1386347 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>COCCOC>[C:12]1([C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][C:7](=[O:11])[NH:8]3)=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 27732896-bromo-2,3-dihydro-1H-indol-2-one

Product 1

HCID 105363846-Phenyl-1,3-dihydro-indol-2-oneYield 60%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

6-Bromooxindole (800 mg, 3.8 mmol), (prepared as described for the starting material in Example 62), phenylboronic acid (500 mg, 4.1 mmol) sodium hydrogen carbonate (saturated aqueous solution, 50 ml) and 1,2-dimethoxyethane (100 ml) were mixed together and the solution was degassed using alternatively vacuum and argon. Tetrakis(triphenylphosphine)palladium(0) (50 mg) was added and the solution degassed again before heating it to reflux for 8 hours. The reaction mixture was evaporated to dryness using a rotary evaporator and the solid residue partitioned between water (75 ml) and ethyl acetate (100 ml). The aqueous phase was reextracted with more ethyl acetate (100 ml×3), the organic phases were combined, washed with brine and passed directly through a short plug of silica to remove the baseline impurities. The solvent was evaporated and the solid was triturated in ether and filtered to give 6-phenyloxindole as a pink solid (375 mg, 60%).

Workup

  1. additionwere mixed together
  2. customthe solution was degassed
  3. additionTetrakis(triphenylphosphine)palladium(0) (50 mg) was added
  4. customthe solution degassed again
  5. temperaturebefore heating it
  6. temperatureto reflux for 8 hours
  7. customThe reaction mixture was evaporated to dryness
  8. customa rotary evaporator
  9. customthe solid residue partitioned between water (75 ml) and ethyl acetate (100 ml)
  10. washwashed with brine
  11. customto remove the baseline impurities
  12. customThe solvent was evaporated
  13. customthe solid was triturated in ether
  14. filtrationfiltered

Sources & evidence

ORD record
ord-df3653d3650f499cae41ae061ee09889
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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