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Chlorotriethylsilane → 2-Bromo-7-(pyridin-3-yl)triethylsilyloxymethylimidazo[5,1-b]thiazole

HRID 230035
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 230035
C(N(C(C)C)CC)(C)C.[CH2:10]([Si:12](Cl)([CH2:15][CH3:16])[CH2:13][CH3:14])[CH3:11].[Br:18][C:19]1[S:23][C:22]2=[C:24]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[N:25]=[CH:26][N:21]2[C:20]=1[CH2:33][OH:34]>CN(C)C=O.C(OCC)(=O)C>[Br:18][C:19]1[S:23][C:22]2=[C:24]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[N:25]=[CH:26][N:21]2[C:20]=1[CH2:33][O:34][Si:12]([CH2:15][CH3:16])([CH2:13][CH3:14])[CH2:10][CH3:11]
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Komponenten

6

Edukt 3

HCID 13819ChlorotriethylsilaneHCID 81531DiisopropylethylamineHCID 230887952-Bromo-7-(pyridin-3-yl)hydroxymethylimidazo[5,1-b]thiazole

Produkt 1

HCID 688224232-Bromo-7-(pyridin-3-yl)triethylsilyloxymethylimidazo[5,1-b]thiazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

Diisopropylethylamine (3.1 ml) and 3.0 ml of triethylsilylchloride were added in that order to a solution of 4.05 g of 2-bromo-7-(pyridin-3-yl)hydroxymethylimidazo[5,1-b]thiazole in 30 ml of dimethylformamide, and the mixture was stirred at room temperature for one hr. The reaction mixture was diluted with ethyl acetate, and the diluted reaction mixture was washed with water, a 5% aqueous sodium bicarbonate solution, and a 20% aqueous sodium chloride solution in that order and was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and the residue was purified by column chromatography on silica gel (2 to 5% methanol/methylene chloride) to give 5.14 g of 2-bromo-7-(pyridin-3-yl)triethylsilyloxymethylimidazo[5,1-b]thiazole.

Aufarbeitung

  1. customthe diluted reaction mixture
  2. washwas washed with water
  3. dry with materiala 5% aqueous sodium bicarbonate solution, and a 20% aqueous sodium chloride solution in that order and was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by evaporation
  5. customthe residue was purified by column chromatography on silica gel (2 to 5% methanol/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-ef6214dcf1694e91a8d125533de12e6e
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07563901B2

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