Dimethylformamide → Ethyl 7-chloro-2-methyl-2H-pyrazolo[4,3-b]pyridine-6-carboxylate

HRID 1731294

Reaktionsgleichung

Reaktionsgleichung von HRID 1731294
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[CH:13]=[N:14][NH:15][C:3]=12.[CH3:16]N(C)C=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]2[C:4](=[CH:13][N:14]([CH3:16])[N:15]=2)[N:5]=[CH:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Komponenten

4

Edukt 2

HCID 6228DimethylformamideHCID 20038759Ethyl 7-chloro-1H-pyrazolo[4,3-B]pyridine-6-carboxylate

Produkt 1

HCID 20228780Ethyl 7-chloro-2-methyl-2H-pyrazolo[4,3-b]pyridine-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Ethyl 7-chloro-1H pyrazolo[4,3-b]pyridine-6-carboxylate (4.5 g, 0.02 mole) and dimethyl formamide demethylacetal2 (10 ml, 0.04 mole) in dry toluene (200 ml) were heated together under reflux for 1 h. The solvent and excess of reagent were distilled off under reduced pressure to give a brown oil containing two isomers. The 1-methyl3 and 2-methyl isomers were separated by column chromatography on silica gel with ethyl acetate as eluant to give the title compound as a white crystalline solid m.p. 118°-120° C.

Aufarbeitung

  1. temperatureunder reflux for 1 h
  2. distillationThe solvent and excess of reagent were distilled off under reduced pressure
  3. customto give a brown oil
  4. additioncontaining two isomers
  5. customThe 1-methyl3 and 2-methyl isomers were separated by column chromatography on silica gel with ethyl acetate as eluant

Quellen und Nachweise

ORD-Eintrag
ord-48c847953c444c598162436ed014f25c
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04621089

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