Ethyl chloroacetate → Ethyl (3-iodo-1H-pyrazolo[3,4-b]pyridin-1-yl)acetate

HRID 390558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390558
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C.C(OCC)(=O)C>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:3]=1

Komponenten

6

Edukt 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 178506575HCID 178506575, Verbindung

Produkt 1

HCID 57642768Ethyl (3-iodo-1H-pyrazolo[3,4-b]pyridin-1-yl)acetateAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 3-iodo-1H-pyrazolo[3,4-b]pyridine (9.8 g, 40 mmol, 1 equiv) and potassium carbonate (27.6 g, 5 equiv) in 15 mL of DMF at 90° C. was added ethyl chloroacetate (8.5 mL, 40 mmol, 1 equiv). Two hours later, the reaction mixture was diluted with ethyl acetate followed by washing with saturated aqueous NaHCO3. The organic layer was dried and concentrated to provide the crude product. Purification of the crude product by flash chromatography gave ethyl (3-Iodo-pyrazolo[3,4-b]pyridin-1-yl)-acetate (11 g).

Aufarbeitung

  1. washby washing with saturated aqueous NaHCO3
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customto provide the crude product
  5. customPurification of the crude product by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-15c23fcd97c04de490af34c0ed1b3269
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383630B2

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