Benzyl Bromide → 2-Benzyl-6-bromo-2H-indazole

HRID 1850039

Reaktionsgleichung

Reaktionsgleichung von HRID 1850039
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C>O1CCOCC1>[CH2:11]([N:7]1[CH:6]=[C:5]2[C:9]([CH:10]=[C:2]([Br:1])[CH:3]=[CH:4]2)=[N:8]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 178424716-Bromo-1H-indazole

Produkt 1

HCID 585296892-Benzyl-6-bromo-2H-indazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

6-Bromoindazole (3.63 g, 18 mmol) was suspended in dioxane (15 mL) and benzyl bromide (2.65 mL, 22 mmol, 1.2 eq.) was added. The reaction was heated to reflux overnight, then allowed to cool to 80° C. after which point ethyl acetate (50 mL) added. The cake was broken up with a spatula and after stirring for 20 min, the solids were filtered off and washed with ethyl acetate, giving glossy white crystals of the hydrobromide salt of 2-benzyl-6-bromoindazole. These were suspended in ethyl acetate (100 mL) and shaken with saturated NaHCO3 (150 mL) until dissolution. The layers were separated and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layers were concentrated to an off-white powder which was recrystallized from 66% ethanol (40 mL). Washing with water and drying in vacuo gave 2-benzyl-6-bromoindazole (3.30 g, 62%) as shiny white plates.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. additionadded
  4. filtrationthe solids were filtered off
  5. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9f201dd0cce546afaab84d6a390c9720
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957049B2

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