Chen Ying-qi
2008
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Journal
Journal of Chemical Engineering of Chinese Universities
Abstract
2-Amino-5-fluoropyridine is an important intermediate for the synthesis of LBM415 which is the peptide deformylas inhibitor. Using 2-aminopyridine as raw material and via nitrification,amino acetylation,reduction of nitro,diazolization,Schiemann reaction and hydrolysis of acetyl,a novel synthesis route of 2-amino-5-fluoropyridine was proposed. Comparing with the 2-amino-5-fluoropyridine synthesis methods reported in literatures,the proposed route simplifies the experimental operations,has no need for the synthesis of 2-chloro-5-aminopyridine which is the raw material of the reported method,avoids the difficulties in separating the intermediate products of the reported method and solves the problems of low yield and low purity of the final product synthesized by the reported method. The optimal reaction conditions (temperature,time and molar yield) of the proposed route were found as follows. Nitrification: 45℃,2 h and 41%; amino acetylation: reflux,1 h and 96.3%; reduction of nitro: reflux,1 h and 90%; diazolization: -5~0℃,2 h and 81.4%; Schiemann reaction:130℃,0.5 h; hydrolysis of acetyl: reflux,2.5 h and the total yield of final two steps is 51.6%. The melting point of the product obtained by the proposed route was found to be the same of those reported in literatures,and the structure of the target product was affirmed by 1H-NMR and IR.