Sodium Carbonate → 6-Phenyl-1,3-dihydro-indol-2-one

HRID 1007376Notes

Reaction equation

HRID 1007376 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(OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C>[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

6

Reactant 3

HCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 27732896-bromo-2,3-dihydro-1H-indol-2-one

Product 1

HCID 105363846-Phenyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

2.4 g of 6-bromo-2-indolinone are placed in 60 ml of dimethoxyethane, 1.9 g of phenylboric acid in 8 ml of ethanol and 0.3 g of tetrakistriphenylphosphine palladium are added and to this mixture 12 ml of 2N sodium carbonate solution are added dropwise at ambient temperature. The mixture is stirred for 6 hours at 85° C. After cooling the catalyst is filtered off, the solvent is eliminated and the residue is washed with 100 ml of water and 20 ml of 1N sodium hydroxide solution. The residue is purified through a silica gel column with petroleum ether/ethyl acetate (8:2) as eluant.

Workup

  1. additionare added dropwise at ambient temperature
  2. temperatureAfter cooling the catalyst
  3. filtrationis filtered off
  4. washthe residue is washed with 100 ml of water and 20 ml of 1N sodium hydroxide solution
  5. customThe residue is purified through a silica gel column with petroleum ether/ethyl acetate (8:2) as eluant

Sources & evidence

ORD record
ord-c3f6e35ec8d04909a8eb479871bcf3f7
Source dataset
uspto-grants-2004_09
Patent number
US06794395B1

Reaction notes

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