Palladium-Catalyzed Regioselective Arylation of Imidazo [1, 2-b][1, 2, 4] triazine: Synthesis of an α2/3-Selective GABA Agonist

…, PN Devine, RA Desmond, RH Szumigala…

Index: Gauthier Jr., Donald R.; Limanto, John; Devine, Paul N.; Desmond, Richard A.; Szumigala Jr., Ronald H.; Foster, Bruce S.; Volante Journal of Organic Chemistry, 2005 , vol. 70, # 15 p. 5938 - 5945

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Citation Number: 47

Abstract

A convergent, practical, and efficient synthesis of 2', 6-difluoro-5'-[3-(1-hydroxy-1- methylethyl) imidazo [1, 2-b][1, 2, 4] triazin-7-yl] biphenyl-2-carbonitrile (1), an orally active GABAA α2/3-selective agonist, is described. The seven-step, chromatography-free synthesis was demonstrated on a multi-kilogram scale and utilized biaryl bromide 6 and imidazotriazine 22 as key intermediates. Biaryl bromide 6 was prepared via a highly ...