Monday, June 30, 2008
Emerald Grand Ballroom (Sheraton Burlington Hotel and Conference Center)
282

Palladium Catalyzed Direct Heck Coupling at C-5 of Imidazo[1,5-a]Pyrazines

Jian-Xin Wang1, J. Adam McCubbin1, Meizhong Jin2, Andrew P. Crew2, Radoslaw S. Laufer2, Mark J. Mulvihill2, Victor Snieckus1, and Johnathan Board3. (1) Queens University, Kingston, ON, Canada, (2) OSI Pharmaceuticals Inc, Farmingdale, NY, (3) Queen's University, Kingston, ON, Canada

A regioselective oxidative Heck C-5 reaction for imidazo[1,5-a]pyrazines has been uncovered. The reaction is optimal under Pd-catalyzed conditions using the Fu ligand and shows good generality with respect to a variety of electron rich and poor aromatic aryl bromides and aryl iodides. The scope of this direct Heck process has also been examined for readily available C-8 substituted imidazo[1,5-a]pyrazines, (R = NH2, NMe2, OMe) and aromatic analogues derived from Suzuki cross coupling reactions.


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