Hydrochloric Acid → Ethyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 1521699

Reaktionsgleichung

Reaktionsgleichung von HRID 1521699
Cl.[Cl:2][C:3]1[N:8]=[C:7]2[NH:9][C:10]([C:12]([OH:14])=[O:13])=[CH:11][C:6]2=[CH:5][CH:4]=1.[CH2:15](O)[CH3:16]>>[Cl:2][C:3]1[N:8]=[C:7]2[NH:9][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:11][C:6]2=[CH:5][CH:4]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 219765806-Chloro-1H-pyrrolo(2,3-b)pyridine-2-carboxylic acid

Produkt 1

HCID 21868758Ethyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylateAusbeute 25 %

Versuchsvorschrift

HCl gas is bubbled through a solution of 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (36 g, 183 mmol) in ethanol (500 mL) at 0° C. for 30 min. The reaction mixture is then heated at reflux for 16 h. The solvent is evaporated and the residue is diluted with CH2Cl2 and filtered. The filtrate is evaporated and the residue is washed with diethyl ether (2×250 mL). The organic layers are dried (Na2SO4) and concentrated. The crude residue is purified by passing through the column of neutral alumina, eluting with 10% EtOAc/hexane to afford the title compound as a white solid (10 g, 25%).

Aufarbeitung

  1. temperatureThe reaction mixture is then heated
  2. temperatureat reflux for 16 h
  3. customThe solvent is evaporated
  4. additionthe residue is diluted with CH2Cl2
  5. filtrationfiltered
  6. customThe filtrate is evaporated
  7. washthe residue is washed with diethyl ether (2×250 mL)
  8. dry with materialThe organic layers are dried (Na2SO4)
  9. concentrationconcentrated
  10. customThe crude residue is purified
  11. washeluting with 10% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-2661df0607a840af8a7e0181cc9a53ae
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073926B2

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