Potassium Carbonate → HCID 20708409, compound

HRID 430781Notes

Reaction equation

HRID 430781 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[C:8]([O:13]CC3C=CC=CC=3)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.[H][H].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]([O:33][CH3:34])=[O:32].[Cl-].[NH4+]>C(O)C.CN(C=O)C.[Pd]>[OH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[C:8]([O:13][CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 18351734HCID 18351734, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20708409HCID 20708409, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

Under argon atmosphere, 1-(2-hydroxyethyl)-4-benzyloxyindoline (369 mg) was dissolved in ethanol and the obtained solution was stirred at room temperature. To this solution, 5% Pd/C (46 mg) was added and the atmosphere in the reaction vessel was replaced with hydrogen. After confirming vanishment of the materials, the atmosphere of the reaction vessel was replaced with argon. Solids were removed by filtration through Celite and the solvent was removed under reduced pressure to obtain a crude product. The crude product was dissolved in DMF and the obtained solution was stirred at room temperature. To this solution, potassium carbonate (368 mg) and methyl bromoacetate (0.26 ml) were added and the mixture was stirred at room temperature. After confirming vanishment of the materials, saturated aqueous ammonium chloride solution (5 ml) was added to the reaction solution and the resultant was extracted three times with ethyl acetate (10 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/1) using silica gel to obtain the desired compound (151 mg, yield: 45%).

Workup

  1. customSolids were removed by filtration through Celite
  2. customthe solvent was removed under reduced pressure
  3. customto obtain a crude product
  4. stirringthe obtained solution was stirred at room temperature
  5. stirringthe mixture was stirred at room temperature
  6. additionwas added to the reaction solution
  7. extractionthe resultant was extracted three times with ethyl acetate (10 ml)
  8. washwashed with saturated brine
  9. dry with materialby drying over sodium sulfate
  10. customAfter removing the sodium sulfate
  11. filtrationby filtration
  12. customthe solvent was removed under reduced pressure
  13. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-46f9fea8a50944e4992d935cc2dffecc
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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