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Sodium Iodide → 2-Bromo-1-[3-(t-butyldimethylsilanyloxy)-2-(tetrahydropyran-2-yloxy)propyl]-4-nitroimidazole

HRID 1092894
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1092894
[Br:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[Si:10]([O:17][CH2:18][CH:19]([O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[CH2:20]Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[Br:1][C:2]1[N:3]([CH2:20][CH:19]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH2:18][O:17][Si:10]([C:13]([CH3:16])([CH3:14])[CH3:15])([CH3:12])[CH3:11])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 477542-Bromo-4-nitroimidazoleHCID 230802371-(t-Butyldimethylsilanyloxy)-3-chloro-2-(tetrahydropyran-2-yloxy)propane

Produkt 1

HCID 230802502-Bromo-1-[3-(t-butyldimethylsilanyloxy)-2-(tetrahydropyran-2-yloxy)propyl]-4-nitroimidazoleAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

2-Bromo-4-nitroimidazole (7.63 g) and 1-(tert-butyldimethylsilanyloxy)-3-chloro-2-(tetrahydropyran-2-yloxy)propane (12 g) were dissolved in N,N-dimethylformamide (80 ml), then potassium carbonate (6.6 g) and sodium iodide (6.3 g) were added thereto, and the reaction mixture was heated and stirred at 110° C. for 12 hours. Ice-water (240 ml) was added, extracted twice with ethyl acetate (150 ml), and the extracts were combined together and washed with an aqueous solution being saturated with sodium chloride (100 ml), then dried over anhydrous magnesium sulfate. After being filtrated under a reduced pressure, the filtrate was concentrated under a reduced pressure. The residue obtained was purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=100/1), there was obtained 2-bromo-1-[3-(t-butyldimethylsilanyloxy)-2-(tetrahydropyran-2-yloxy)propyl]-4-nitroimidazole (12.69 g, yield: 68.7%)

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. extractionextracted twice with ethyl acetate (150 ml)
  3. washwashed with an aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter being filtrated under a reduced pressure
  6. concentrationthe filtrate was concentrated under a reduced pressure
  7. customThe residue obtained
  8. customwas purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=100/1)

Quellen und Nachweise

ORD-Eintrag
ord-39de142f40cc4c6e862d3c1c2baab195
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08129544B2

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