Ethyl bromoacetate → HCID 86680396, Verbindung

HRID 1023155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1023155
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 86680396HCID 86680396, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-43895b6965f043159ec04e10b3a07876
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722670B2

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