Palladium-catalyzed regioselective arylation of imidazo[1,2-b][1,2,4]triazine: synthesis of an alpha 2/3-selective GABA agonist

• Published in: Journal of organic chemistry Vol. 70; no. 15; pp. 5938 - 5945
• Main Authors: Gauthier, Jr, Donald R, Limanto, John, Devine, Paul N, Desmond, Richard A, Szumigala, Jr, Ronald H, Foster, Bruce S, Volante, R P
• Format: Journal Article
• Language: English
• Published: United States 22.07.2005
• Subjects: Acetaldehyde - analogs & derivatives; Acetaldehyde - chemistry; Bromides - chemistry; Catalysis; GABA Agonists - chemical synthesis; Hydrocarbons, Aromatic - chemistry; Imidazoles - chemistry; Palladium - chemistry; Receptors, GABA-A; Stereoisomerism; Structure-Activity Relationship; Triazines - chemical synthesis; Triazoles - chemistry

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 GABA(A) alpha(2/3)-selective agonist, is described. The seven-step, chromatography-free synthesis was demonstrate...