Cyclohexyl bromide → ethyl 6-bromo-1-cyclohexyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 1501602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1501602
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]2[CH:10]=[N:9][NH:8][C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]2[CH:10]=[N:9][N:8]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 7960Cyclohexyl bromideHCID 11430Potassium CarbonateHCID 59766670ethyl 6-bromo-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Produkt 1

HCID 86703425ethyl 6-bromo-1-cyclohexyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Ethyl 6-bromo-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (1 equiv.) was suspended in acetonitrile and K2CO3 (1.5 equiv.) and bromocyclohexane (2 equiv.) was added to it. The reaction mixture was refluxed for 8 h. On completion, acetonitrile was removed under reduced pressure and water was added to it. Extraction was carried out using ethyl acetate; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and residue was purified by silica gel column chromatography to obtain the desired intermediate.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. customOn completion, acetonitrile was removed under reduced pressure and water
  3. additionwas added to it
  4. extractionExtraction
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customSolvent was removed under reduced pressure and residue
  8. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-636a568e2ab94a1fa19ea95e3ab31395
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206157B2

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