Ethyl bromopyruvate → Ethyl 7-ethylimidazo[1,2-a]pyridine-2-carboxylate

HRID 704621

Reaktionsgleichung

Reaktionsgleichung von HRID 704621
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[CH2:8]([C:6]1[CH:5]=[CH:4][N:3]2[CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:1]=[C:2]2[CH:7]=1)[CH3:9]

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 1184254-Ethylpyridin-2-amine

Produkt 1

HCID 20072849Ethyl 7-ethylimidazo[1,2-a]pyridine-2-carboxylateAusbeute 18,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-4-ethylpyridine (3.8 g), ethyl 3-bromo-2-oxopropionate (6.84 g) and ethanol (30 ml) was refluxed for 6 hours. After the reaction mixture was concentrated, water (30 ml) and ehtyl acetate (30 ml) were added to the residue. The mixture was made basic with an aqueous solution of potassium carbonate, and the separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated and the residue was subjected to a column chromatography on silica gel (150 g) and eluted with 15% solution of ethyl acetate in chloroform. The fractions containing the object compound were combined and concentrated to give ethyl 7-ethylimidazo[1,2-a]pyridine-2-carboxylate (1.26 g).

Aufarbeitung

  1. temperaturewas refluxed for 6 hours
  2. concentrationAfter the reaction mixture was concentrated
  3. additionwater (30 ml) and ehtyl acetate (30 ml) were added to the residue
  4. washthe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. washeluted with 15% solution of ethyl acetate in chloroform
  8. additionThe fractions containing the object compound
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-813225852fa145a39cf7ab9cac993ee1
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988698

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