8-Hydroxyquinoline → 1-(2-(4-ethoxyphenyl)thiazol-5-yl)-3,5-dimethylpyridin-2(1H)-one

HRID 56087

反応式

HRID 56087 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].OC1C=CC=C2C=1N=CC=C2.[CH3:18][C:19]1[C:20](=[O:26])[NH:21][CH:22]=[C:23]([CH3:25])[CH:24]=1.Br[C:28]1[S:32][C:31]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH3:41])=[CH:35][CH:34]=2)=[N:30][CH:29]=1>CS(C)=O.[Cu]I>[CH2:40]([O:39][C:36]1[CH:35]=[CH:34][C:33]([C:31]2[S:32][C:28]([N:21]3[CH:22]=[C:23]([CH3:25])[CH:24]=[C:19]([CH3:18])[C:20]3=[O:26])=[CH:29][N:30]=2)=[CH:38][CH:37]=1)[CH3:41]

参加物

7

反応物 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 123485383,5-Dimethyl-1,2-dihydropyridin-2-oneHCID 821347985-Bromo-2-(4-ethoxyphenyl)thiazole

生成物 1

HCID 729508471-(2-(4-ethoxyphenyl)thiazol-5-yl)-3,5-dimethylpyridin-2(1H)-one収率 26%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

A mixture of CuI (0.038 g, 0.20 mmol), Cs2CO3 (0.98 g, 3.00 mmol) and 8-hydroxyquinoline ligand (0.029 g, 0.20 mmol) in DMSO (2 mL) was stirred at rt for 30 min under N2. Then to the reaction mixture was added a solution of 3,5-dimethylpyridin-2(1H)-one (0.30 g, 2.40 mmol) and 5-bromo-2-(4-ethoxyphenyl)thiazole (0.57 g, 2.00 mmol) in DMSO (2 mL) via syringe. The reaction mixture was heated at 130° C. for 12 h, then cooled to rt and filtered. The filtrate was diluted with H2O (10 mL) and extracted with CH2Cl2 (20 mL×3). The combined organic phases were concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:10) to give the title compound (0.17 g, 26%). The compound was characterized by the following spectroscopic data:

後処理

  1. temperatureThe reaction mixture was heated at 130° C. for 12 h
  2. temperaturecooled to rt
  3. filtrationfiltered
  4. additionThe filtrate was diluted with H2O (10 mL)
  5. extractionextracted with CH2Cl2 (20 mL×3)
  6. concentrationThe combined organic phases were concentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:10)

出典と根拠

ORDレコード
ord-0282cdf79cd446d2ad73ec2520a83efd
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

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