Ethyl bromoacetate → HCID 86680396, compound

HRID 1023155Notes

Reaction equation

HRID 1023155 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C1CCN2C(=NCCC2)CC1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CC(O)C>[O:11]=[C:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([O:1][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:3]=2)[NH:7]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 769555-HydroxyoxindoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 86680396HCID 86680396, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 5-hydroxyindolin-2-one (1 g, 6.70 mmol) in 2-Propanol (10 mL) was added DBU (1.52 mL, 10.06 mmol) and ethyl bromoacetate (1.12 mL, 10.06 mmol) at room temperature. The reaction mixture was refluxed at 80° C. for 12 h. After completion of the reaction as monitored by TLC, the reaction mixture was concentrated and water (100 mL) was added. The solid which precipitated was filtered and dried to yield ethyl 2-((2-oxoindolin-5-yl)oxy)acetate as an off white solid (0.75 g, 47.6%) LCMS: RT 0.67 min. LCMS (ES-API), m/z 236.0 (M+H).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated
  3. additionwater (100 mL) was added
  4. customThe solid which precipitated
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-43895b6965f043159ec04e10b3a07876
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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