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

HRID 1072331

反応式

HRID 1072331 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-767fb4c398f54227959bb299765b6475
出典データセット
uspto-grants-2005_06
特許番号
US06908913B2

関連ノート

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