Potassium Carbonate → Ethyl 2-(4-chloro-2-oxopyridin-1(2H)-yl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 43727

反応式

HRID 43727 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([OH:8])[CH:3]=1.Br[C:10]1[S:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:13]([CH3:15])[N:14]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>CN(C=O)C.C(OCC)(=O)C.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C:10]2[S:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:13]([CH3:15])[N:14]=2)[C:4](=[O:8])[CH:3]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylateHCID 178516186HCID 178516186、化合物

生成物 1

HCID 67548707Ethyl 2-(4-chloro-2-oxopyridin-1(2H)-yl)-4-methyl-1,3-thiazole-5-carboxylate収率 0.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

4-Chloro-2-hydroxypyridine (500 mg, 3.86 mmol), ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate (1.06 g, 4.24 mmol), potassium carbonate (1.06 g, 7.67 mmol) and copper (I) iodide (73 mg, 0.38 mmol) were suspended in DMF (4 mL). trans(±)-N,N′-Dimethylcyclohexane-1,2-diamine (82 mg, 0.58 mmol) was added, and the mixture was stirred at 100° C. for five hours. The reaction solution was diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1→2/1) to obtain 3.2 mg of the title compound as a white solid (0.3%).

後処理

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1→2/1)

出典と根拠

ORDレコード
ord-ff16bee848534c6db0aa6f86f3abaec4
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

関連ノート

読み込み中…