Reaktion #72005

Reaktionsgleichung

4-Chloro-2-hydroxypyridine

potassium carbonate

trans(±)-N,N′-Dimethylcyclohexane-1,2-diamine

ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

→

title compound

Ausbeute 0.3%

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

Ausbeute 0.3%

Lösungsmittel

DMF

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water
2. 2
   Trocknendried over anhydrous sodium sulfate
3. 3
   Einengenconcentration under reduced pressure
4. 4
   Sonstigethe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1→2/1)

Vorschrift

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%).

Quelle