Stannane, tributyl(1-ethoxyethenyl)- → 1-(5-Methyl-1H-pyrazolo[3,4-c]pyridin-3-yl)-ethanone

HRID 1527270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527270
Br[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([Sn](CCCC)(CCCC)[C:17]([O:19]CC)=[CH2:18])CCC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:11][C:8]1[CH:9]=[C:10]2[C:2]([C:17](=[O:19])[CH3:18])=[N:3][NH:4][C:5]2=[CH:6][N:7]=1

Komponenten

5

Edukt 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 178421791HCID 178421791, Verbindung

Produkt 1

HCID 682840311-(5-Methyl-1H-pyrazolo[3,4-c]pyridin-3-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-bromo-5-methyl-1H-pyrazolo[3,4-c]pyridine (2.13 g, 10.04 mmol), tri-butyl(1-ethoxyvinyl)tin (6.78 mL, 20.09 mmol) and PdCl2(PPh3)2 (0.705 mg, 1 mmol) in DMF (12.6 mL) was heated at 80° C. overnight under argon atmosphere. Then concentrated under reduced pressure and diluted with EtOAc. HCl (2N) was added, the layers were separated and the aqueous layer was basified by addition of NaHCO3 (1N in water) and extracted with EtOAc (3×). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The yellow oil thus obtained was used without further purification in the next step. TLC, Rf (c-hexane/EtOAC 1:1)=0.05; MS (UPLC/MS): 176 [M+H]+, 174 [M−H]−.

Aufarbeitung

  1. concentrationThen concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. additionHCl (2N) was added
  4. customthe layers were separated
  5. additionthe aqueous layer was basified by addition of NaHCO3 (1N in water)
  6. extractionextracted with EtOAc (3×)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe yellow oil thus obtained
  11. customwas used without further purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-64de0387def442e2af14790bfd63a406
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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