Potassium Carbonate → 7-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-6-oxiranylmethoxy-1H-indazole

HRID 1815962

Reaktionsgleichung

Reaktionsgleichung von HRID 1815962
[Br:1][C:2]1[C:3]([OH:22])=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C@@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH3:13])[N:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:29]([CH:31]1[O:33][CH2:32]1)Br>CC(C)=O>[Br:1][C:2]1[C:3]([O:22][CH2:29][CH:31]2[CH2:32][O:33]2)=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C@@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])[CH3:13])[N:8]=[CH:7]2

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 1364116817-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-ol

Produkt 1

HCID 867596497-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-6-oxiranylmethoxy-1H-indazoleAusbeute 471,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A suspension of the product from Step C (3.66 g, 9.51 mmol), potassium carbonate (1.92 g, 1.46 mmol), and epibromohydrine (1.32 mL, 1.60 mmol) in acetone (200 mL) was heated at reflux for 30 h. The solid was removed by filtration and the filtrate was concentrated to an oil that was purified by chromatography (silica, 2% to 10% EtOAc/hexane) to afford an oil (3.33 g, 79%): LC/MS (+APCI) m/z 441, 443 (M+H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 30 h
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated to an oil that
  5. customwas purified by chromatography (silica, 2% to 10% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ea57fbdc0e21441aa0466e4cc13e11a3
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06881749B2

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