Sodium ethoxide → ethyl 3-amino-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

HRID 2264903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264903
CC[C:3]1[C:8]([C:9]#[N:10])=[C:7]([NH:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:5][N:4]=1.[O-][CH2:17][CH3:18].[Na+]>CCO.O>[CH2:17]([O:15][C:13]([C:12]1[NH:11][C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:8]=2[C:9]=1[NH2:10])=[O:14])[CH3:18]

Komponenten

5

Edukt 2

HCID 2723922Sodium ethoxideHCID 67212023Ethyl-4-(3-cyanopyridine)glycinate

Produkt 1

HCID 23218185ethyl 3-amino-1H-pyrrolo[3,2-c]pyridine-2-carboxylateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of ethyl-4-(3-cyanopyridine)glycinate (2.47 g, 12.1 mmol) under nitrogen in EtOH (60 mL) was added sodium ethoxide (0.90 g, 13.3 mmol) and the mixture was heated at reflux for 1 hour. The mixture was allowed to cool to ambient temperature then quenched by the addition of water (3 mL) and saturated ammonium chloride solution (5 mL). The solvent was concentrated in vacuo, to provide a residue that was diluted with water (30 mL), and extracted with EtOAc (2×40 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated to give the title compound as a brown solid (1.35 g, 55%). LCMS (method B): RT=0.61 min, M+H+=206.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customthen quenched by the addition of water (3 mL) and saturated ammonium chloride solution (5 mL)
  4. concentrationThe solvent was concentrated in vacuo
  5. customto provide a residue that
  6. extractionextracted with EtOAc (2×40 mL)
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-45af08c7d9864d7e8e1a48054187e9c9
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855216B2

Notizen zur Reaktion

Wird geladen…