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Direct Synthesis of Fluorinated Heteroarylether Bioisosteres

Authors


  • Financial support for this work was provided by the NIH/NIGMS (GM-073949), Eisai, the Binational US-Israel Science Foundation, and the Frost Foundation (to D.S). We are grateful to P. Siva (Bristol-Myers Squibb) for the calculations shown in Scheme 1 A, to J. Kadow (Bristol-Myers Squibb) for a sample of 36, and to T. Ryba and C. Thomas (Sigma–Aldrich) for a donation of chemicals. The Uehara Memorial Foundation and SIOC provided funding for postdoctoral fellowships to Y.F. and Q.Z., respectively.

Abstract

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(Bioiso)steering in a new direction: A modular synthesis of reagents (e.g. sodium difluoroethylsulfinate) that can be used for the direct incorporation of difluoroalkyl groups onto heterocycles is reported. The scope and generality of the incorporation of difluoroalkyl groups is exemplified with the difluoroethyl group and a proof of principle is shown for a general synthesis of fluorinated heteroarylether bioisosteres.

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