p-Toluenesulfonic acid → 7-bromo-2-methyl-3-((E)-1-propyl-but-1-enyl)-2H-indazole

HRID 902554

Reaktionsgleichung

Reaktionsgleichung von HRID 902554
[Br:1][C:2]1[C:10]2[C:6](=[C:7]([C:12](O)([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:10]2[C:6](=[C:7](/[C:12](/[CH2:16][CH2:17][CH3:18])=[CH:13]/[CH2:14][CH3:15])[N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 210945894-(7-bromo-2-methyl-2H-indazol-3-yl)-heptan-4-ol

Produkt 1

HCID 597023557-bromo-2-methyl-3-((E)-1-propyl-but-1-enyl)-2H-indazoleAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 4-(7-bromo-2-methyl-2H-indazol-3-yl)-heptan-4-ol (1.75 g, 5.38 mmol), 50 mL of toluene, and 4-toluenesulfonic acid (1.23 g, 6.46 mmol) was stirred at 110° C. for 20 h, then allowed to cool. A saturated aqueous NaHCO3 solution (50 mL) was added, and the mixture was extracted with three 30 mL portions of ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated to a brown oil. Column chromatography (0→8% EtOAc/hexanes) afforded of 7-bromo-2-methyl-3-((E)-1-propyl-but-1-enyl)-2H-indazole (43; 1.47 g; 89%).

Aufarbeitung

  1. temperatureto cool
  2. extractionthe mixture was extracted with three 30 mL portions of ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-fb67c054dff641d6b20006099f1dc5c3
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365211B2

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