Ethyl (chloroformyl)acetate → Ethyl 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate

HRID 79415

Reaktionsgleichung

Reaktionsgleichung von HRID 79415
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.Cl[CH:11]([CH:17]=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][N:1]=2)[CH:4]=1)#[N:9]

Komponenten

4

Edukt 2

HCID 118030Ethyl (chloroformyl)acetateHCID 8182602-Amino-5-cyanopyridine

Produkt 1

HCID 67259960Ethyl 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Amino-5-cyanopyridine (15.5 g, 152 mmol) was dissolved in ethanol (500 mL) in 2 L round bottom flask. Ethyl 2-chloro-3-oxopropanoate (5% in benzene; 730 mL; Commercial solution from Toronto Research Chemicals Inc.) was added and the mixture was heated at reflux for 10 hours. The mixture was concentrated under reduced pressure and the residue was purified by silica-gel chromatography to give ethyl 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate as a pale yellow solid (13.9 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 10 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica-gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-adaaded92f22460997bcf9986839f158
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

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