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Water → 7-[[5-(t-Butyldimethylsilyloxymethyl)pyridin-3-yl]hydroxymethyl]imidazo[5,1-b]thiazole

HRID 1072331
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1072331
Br[C:2]1[CH:3]=[C:4]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:5]=[N:6][CH:7]=1.C([Li])CCC.CCCCCC.[CH:28]([C:30]1[N:31]=[CH:32][N:33]2[CH:37]=[CH:36][S:35][C:34]=12)=[O:29].O>C(OCC)C.C1COCC1>[Si:10]([O:9][CH2:8][C:4]1[CH:3]=[C:2]([CH:28]([OH:29])[C:30]2[N:31]=[CH:32][N:33]3[CH:37]=[CH:36][S:35][C:34]=23)[CH:7]=[N:6][CH:5]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]
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Komponenten

7

Edukt 4

HCID 962WaterHCID 219840913-Bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)pyridineHCID 22390357Imidazo(4,3-b)(1,3)thiazole-7-carbaldehydeHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 223903777-[[5-(t-Butyldimethylsilyloxymethyl)pyridin-3-yl]hydroxymethyl]imidazo[5,1-b]thiazoleAusbeute 36,9 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2.49 g of 5-bromo-3-(t-butyldimethylsilyloxymethyl)pyridine in 25 ml of dry diethyl ether was cooled to −85° C. under an argon atmosphere, and 5.56 ml of a 1.57 N n-butyllithium/hexane solution was added dropwise to the cooled solution over a period of 10 min. The mixture was stirred at that temperature for 30 min, and a solution of 881 mg of 7-formylimidazo[5,1-b]thiazole in 20 ml of dry THF was then added thereto, followed by further mixing at the same temperature for 30 min. Water was added to the reaction solution. The mixture was extracted three times with chloroform. The organic layer was dried over anhydrous magnesium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol=10:1) to give 803 mg of 7-[[5-(t-butyldimethylsilyloxymethyl)pyridin-3-yl]hydroxymethyl]imidazo[5,1-b]thiazole.

Aufarbeitung

  1. additionby further mixing at the same temperature for 30 min
  2. extractionThe mixture was extracted three times with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationwas then concentrated under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-767fb4c398f54227959bb299765b6475
Quelldatensatz
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06908913B2

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