Water → HCID 67976364, Verbindung

HRID 706654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706654
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH3:23])[N:16]=2)[N:3]=1.[C:24](=O)([O-])[O-].[K+].[K+].CB(O)O.O>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:22]([O:21][C:17]1[N:16]=[C:15]([CH2:14][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([CH3:24])=[N:3]2)[CH:20]=[CH:19][CH:18]=1)[CH3:23]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 67976141HCID 67976141, Verbindung

Produkt 1

HCID 67976364HCID 67976364, VerbindungAusbeute 28,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 3-bromo-1-((6-ethoxypyridin-2-yl)methyl)-4-nitro-1H-indazole (0.500 g, 1.33 mmol) in dioxane (0.2M, 7 mL) was treated with potassium carbonate (0.916 g, 6.63 mmol), methylboronic acid (0.793 g, 13.3 mmol), water (0.239 mL, 13.3 mmol), followed by tetrakis(triphenylphosphine)palladium (0) (0.0766 g, 0.0663 mmol) at ambient temperature, purging under argon. The mixture was refluxed overnight, cooled to ambient temperature, filtered through glass fiber filter paper, concentrated and purified on silica (10-75% EtOAc in hexanes) to give 1-((6-ethoxypyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole (0.118 g, 28% yield).

Aufarbeitung

  1. custompurging under argon
  2. temperatureThe mixture was refluxed overnight
  3. filtrationfiltered through glass fiber
  4. filtrationfilter paper
  5. concentrationconcentrated
  6. custompurified on silica (10-75% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9616e6f1db3c4e36afa2181bb6452d4e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174981B2

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