Ethyl bromopyruvate → 2,8-Diethyl imidazo[1,2-a]pyridine-2,8-dicarboxylate

HRID 1440470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1440470
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:10][C:11]1[N:21]=[CH:20][CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(C(C)=O)C>[CH2:7]([O:6][C:4]([C:3]1[N:10]=[C:11]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18][CH:19]=[CH:20][N:21]2[CH:2]=1)=[O:5])[CH3:8]

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 12433260Ethyl 2-aminopyridine-3-carboxylate

Produkt 1

HCID 189838522,8-Diethyl imidazo[1,2-a]pyridine-2,8-dicarboxylateAusbeute 26,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of ethyl bromopyruvate (2.3 g, 10.2 m mol and ethyl 2-aminonicotinate (1.7 g, 10 m mol) in methyl ethyl ketone (17 ml) was refluxed for 5 hours. After completion of the reaction, the mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. The residue to which saturated sodium hydrogen carbonate aqueous solution (50 ml) was added was extracted with chloroform (100 ml×3). The extract was washed with water, dried over MgSO4 and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate) to give the object compound (0.7 g, yield 26.7%) as crystals. m.p. 97° C.

Aufarbeitung

  1. temperaturewas refluxed for 5 hours
  2. customAfter completion of the reaction
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. additionThe residue to which saturated sodium hydrogen carbonate aqueous solution (50 ml) was added
  6. extractionwas extracted with chloroform (100 ml×3)
  7. washThe extract was washed with water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe concentrate was purified by silica gel column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-117e9f0b65764745badc6d7273b6fe6c
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05498774

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