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

HRID 1072331

반응식

HRID 1072331 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 223903777-[[5-(t-Butyldimethylsilyloxymethyl)pyridin-3-yl]hydroxymethyl]imidazo[5,1-b]thiazole수율 36.9%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-767fb4c398f54227959bb299765b6475
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908913B2

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