Development of a Practical Synthesis of Functionalized Azaxanthene-Derived Nonsteroidal Glucocorticoid Receptor Modulators

…, N Cuniere, TM Razler, J Zhu…

Index: Zhu, Jason; Razler, Thomas M.; Xu, Zhongmin; Conlon, David A.; Sortore, Eric W.; Fritz, Alan W.; Demerzhan, Roman; Sweeney, Jason T. Organic Process Research and Development, 2011 , vol. 15, # 2 p. 438 - 442

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Abstract

An efficient route to two functionalized 2-aryl-5 H-chromeno [2, 3-b] pyridines (azaxanthenes) is reported. The addition of lithiated 2, 6-dichloropyridine to salicylaldehyde followed by cyclization was a key process improvement identified for the formation of the azaxanthene core. Further elaboration of 2-chloro-5 H-chromeno [2, 3-b] pyridin-5-ol at the 5 position was accomplished via Lewis acid-catalyzed coupling with commercially available ...