HCID 86692516, compound → HCID 82278766, compound

HRID 1748571Notes

Reaction equation

HRID 1748571 reaction equation
C([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]=[CH2:16])[CH:13]=2)[N:8]([CH3:17])[CH:7]=1)=[O:5])C>C(O)C.[C].[Pd]>[CH2:15]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:17])[CH:7]=[C:6]2[C:4]([OH:5])=[O:3])[CH3:16]

Participants

4

Reactant 1

HCID 86692516HCID 86692516, compound

Product 1

HCID 82278766HCID 82278766, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-methyl-5-vinyl-1H-indole-3-carboxylic acid ethyl ester (934 mg) in ethanol (40 ml) was added 10% palladium carbon (containing about 50% water) (95 mg) at room temperature, and stirred at the same temperature for 4 hours under hydrogen gas flow. After completion of the reaction, the mixture was filtered through Celite, and then the filtrate was concentrated. The obtained residue was dissolved in ethanol (20 ml), 1N aqueous solution of sodium hydroxide (20 ml) was added thereto at room temperature, and stirred at 70° C. for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered through Celite, and then the solvent was evaporated. The obtained residue was extracted with ethyl acetate. To the aqueous layer was added 1 N hydrochloric acid aqueous solution, and the precipitated solid was collected by filtration to give the titled compound (797 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe obtained residue was dissolved in ethanol (20 ml)
  5. addition1N aqueous solution of sodium hydroxide (20 ml) was added
  6. stirringat room temperature, and stirred at 70° C. for 3 hours
  7. customAfter completion of the reaction
  8. filtrationfiltered through Celite
  9. customthe solvent was evaporated
  10. extractionThe obtained residue was extracted with ethyl acetate
  11. additionTo the aqueous layer was added 1 N hydrochloric acid aqueous solution
  12. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-aefeff6e2df9465e8e9b3740f0d0aad6
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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