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Note | Regular issue | Vol 68, No. 1, 2006, pp.167-173
Published online, 1st November, 2005
DOI: 10.3987/COM-05-10569
■ A New Efficient Synthesis of 5-Aryloxazoles from Arylidene Diacetates and Application to the Preparation of BMS-337197, a Novel IMPDH Inhibitor

Bang-Chi Chen,* Mark S. Bednarz, Huiping Zhang, Rulin Zhao, T. G. Murali Dhar, Balu Balasubramanian, and Joel C. Barrish

*Discovery Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, NJ 08543-4000, U.S.A.

Abstract

A new method for the synthesis of 5-aryloxazoles is described. Treatment of arylidene diacetates with one equivalent of TosMIC reagent in the presence of excess of potassium carbonate in methanol afforded 5-aryloxazoles in “one-pot” in 90-94%. Heteroarylidene diacetates reacted in a similar way. Application of the new method to the synthesis of the novel IMPDH inhibitor BMS-337197 is also presented.