Bench-scale synthesis of rosiglitazone

Subject Areas :

ابراهیم کیان مهر ¹ , مارال غلامحسینی ²

1 - دانشیار شیمی آلی، دانشکده شیمی، پردیس علوم، دانشگاه تهران، ایران
2 - دکترای شیمی آلی، دانشکده شیمی، پردیس علوم، دانشگاه تهران، ایران

Received: 2018-09-17 Accepted : 2019-01-16 Published : 2019-02-20

Keywords: Rosiglitazone, Antidiabetic drug, Diabet type 2, Avandia BRL49653,

Abstract :

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.

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