Ethyl bromopyruvate → Ethyl 5-Chloroimidazo[1,2-a]pyridine-2-carboxylate

HRID 1608584

Reaktionsgleichung

Reaktionsgleichung von HRID 1608584
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.Br[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[CH2:15]([O:14][C:12]([C:11]1[N:1]=[C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]2[CH:10]=1)=[O:13])[CH3:16]

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 2062462-Amino-6-chloropyridine

Produkt 1

HCID 12428959Ethyl 5-Chloroimidazo[1,2-a]pyridine-2-carboxylateAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-amino-6-chloropyridine (6.43 g, 50 mmoles) and ethyl bromopyruvate (9.75 g, 50 mmoles) in ethanol (150 ml) was heated at reflux for 4 hours. After the solvent was removed, chloroform was added to the residue, which was washed in turn with saturated sodium bicarbonate and saturated saline, and then dried over anhydrous magnesium sulfate. After the solvent was concentrated, n-hexane was added to the mixture. Then, the crystals precipitated were filtered off and washed with n-hexane to obtain 7.60 g of the desired product (67.6%, pale yellow crystals).

Aufarbeitung

  1. temperatureat reflux for 4 hours
  2. customAfter the solvent was removed
  3. additionchloroform was added to the residue, which
  4. washwas washed in turn with saturated sodium bicarbonate and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationAfter the solvent was concentrated
  7. additionn-hexane was added to the mixture
  8. customThen, the crystals precipitated
  9. filtrationwere filtered off
  10. washwashed with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-9d430efc14f146c992d3c894199849ef
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05395839

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