Potassium Carbonate → Tert-butyl 2-(3-iodo-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

HRID 1527306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527306
[I:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH3:11])[CH:9]=2)[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>C(#N)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH3:11])[CH:9]=2)[N:4]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 178422150HCID 178422150, Verbindung

Produkt 1

HCID 68283706Tert-butyl 2-(3-iodo-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a suspension of 3-iodo-5-methyl-1H-pyrazolo[3,4-c]pyridine (1.00 g, 3.86 mmol), and potassium carbonate (1.28 g, 9.26 mmol) in acetonitrile (40 mL) was added tert-butyl bromoacetate (0.685 mL, 4.63 mmol) dropwise at RT and the resulting mixture was heated to reflux for 16 h. The mixture was cooled to RT and filtered, the solid was washed with acetonitrile and the filtrate was concentrated under vacuum. The residual oil was used directly in the next step without further purification. MS (LC/MS): 374.0 [M+H]+; tR (HPLC conditions k): 2.96 min.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 16 h
  3. filtrationfiltered
  4. washthe solid was washed with acetonitrile
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe residual oil was used directly in the next step without further purification
  7. custom2.96 min.

Quellen und Nachweise

ORD-Eintrag
ord-9ffb9779d5804c4b9560d2eb625536ac
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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