HCID 69060787, compound → Ethyl 1-ethyl-6-hydroxy-1H-indole-3-acetate

HRID 490686Notes

Reaction equation

HRID 490686 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]([C:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16]CC3C=CC=CC=3)=[CH:13][CH:14]=2)[N:9]([CH2:24][CH3:25])[CH:8]=1)=O)[CH3:2]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:7]1[C:15]2[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=2)[N:9]([CH2:24][CH3:25])[CH:8]=1)[CH3:2]

Participants

3

Reactant 1

HCID 69060787HCID 69060787, compound

Product 1

HCID 57675468Ethyl 1-ethyl-6-hydroxy-1H-indole-3-acetateYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(6-Benzyloxy-1-ethyl-1H-indol-3-yl)-oxo-acetic acid ethyl ester (0.843 g, 2.40 mmol) is dissolved in anhydrous dioxane (10 mL) then purged and back filled with nitrogen a few times. Palladium on carbon (10%) (0.200 g, 20% by wt.) is added and the reaction followed by heating to reflux. Slow addition of a saturated solution of sodium hypophosphite is initiated and the reaction is monitored by TLC. After the starting material is completely consumed, the reaction is allowed to cool to room temperature, diluted with dichloromethane and celite added. The mixture is filtered through a plug of celite and the two phases are separated. The organic layer is washed with water and brine, dried over sodium sulfate, then concentrated. The residue is further purified using flash column chromatography. The (1-Ethyl-6-hydroxy-1H-indol-3-yl)-acetic acid ethyl ester (0.564 g, 2.28 mmol) is formed in 95% yield.

Workup

  1. customthen purged
  2. additionback filled with nitrogen a few times
  3. additionPalladium on carbon (10%) (0.200 g, 20% by wt.) is added
  4. temperatureby heating to reflux
  5. additionaddition of a saturated solution of sodium hypophosphite
  6. customAfter the starting material is completely consumed
  7. additiondiluted with dichloromethane and celite
  8. additionadded
  9. filtrationThe mixture is filtered through a plug of celite
  10. customthe two phases are separated
  11. washThe organic layer is washed with water and brine
  12. dry with materialdried over sodium sulfate
  13. concentrationconcentrated
  14. customThe residue is further purified

Sources & evidence

ORD record
ord-e6da8f49c4fb4a2cab723c219668734e
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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