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Paper Information

Journal:   JOURNAL OF APPLIED RESEARCHES IN CHEMISTRY (JARC)   winter 2019 , Volume 12 , Number 4 ; Page(s) 131 To 137.

Bench-scale synthesis of rosiglitazone

Author(s):  Kianmehr Ebrahim*, Gholamhosseyni Maral
* School of Chemistry, College of Science, University of Tehran, Tehran, Iran
In this study, a suitable method for the preparation of Rosiglitazone on laboratory scale using 4-bromo benzaldehyde, 4, 2-thiazolidinedione and 2-chloropyridine, as the starting materials, is presented. In the key step of this four-step process, palladium complexes have been used which significantly increase the reaction efficiency and overall yield compared to previous methods. In the first step, by the reaction of 2-chloropyridine with N-methyl ethanolamine the intermediate compound 2-(methyl (pyridine-2-yl)amino) ethane-1-ol is obtained which is converted to 4-(2-(methyl(pyridine-2-yl)amino)ethoxyl)benzaldehyde in the presence of palladium acetate and 4-bromo benzaldehyde. Finally, the desired product is obtained by condensation reaction of this intermediate with 2, 4-thiazoldinedione followed by reduction.
Keyword(s): Rosiglitazone,Antidiabetic drug,Diabet type 2,Avandia BRL49653
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