Chloroacetaldehyde → Ethyl imidazo[1,2-a]pyridine-8-carboxylate

HRID 1046526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1046526
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[NH2:11])[CH3:2].Cl[CH2:14][CH:15]=O.C([O-])(O)=O.[Na+]>CCO>[CH2:1]([O:3][C:4]([C:5]1[C:6]2[N:7]([CH:14]=[CH:15][N:11]=2)[CH:8]=[CH:9][CH:10]=1)=[O:12])[CH3:2]

Komponenten

5

Edukt 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 12433260Ethyl 2-aminopyridine-3-carboxylate

Produkt 1

HCID 10867135Ethyl imidazo[1,2-a]pyridine-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-nicotinic acid ethyl ester (13.845 g), ClCH2CHO (58 mL), and NaHCO3 (11.85 g) was stirred in EtOH (500 mL) at reflux overnight. The reaction mixture was concentrated, diluted with H2O, and extracted with DCM. The product was purified by ISCO using 100% EtOAc first (to remove unreacted starting material), then using 100% DCM to 5% MeOH/DCM. The product eluted at 3% MeOH/DCM, providing imidazo[1,2-a]pyridine-8-carboxylic acid ethyl ester (10.5 g).

Aufarbeitung

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with H2O
  4. extractionextracted with DCM
  5. customThe product was purified by ISCO
  6. custom100% EtOAc first (to remove unreacted starting material)
  7. washThe product eluted at 3% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-f1c525b73ae34ebfb03b5afdde225f3e
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569306B2

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