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Development of a sp2-sp3 Stille Cross-Coupling for Rapid Synthesis of HIV NNRTI Doravirine Analogues.

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The development of a C(sp2)-C(sp3) cross-coupling reaction for rapid, parallel synthesis of analogues of two HIV NNRTI clinical candidates is described. This method allowed easy access to the C-ring space… Click to show full abstract

The development of a C(sp2)-C(sp3) cross-coupling reaction for rapid, parallel synthesis of analogues of two HIV NNRTI clinical candidates is described. This method allowed easy access to the C-ring space using a practical alkylation with commercially available tributyl(iodomethyl)stannane followed by a palladium-catalyzed coupling with a variety of aryl halides (I, Br) in the presence of copper chloride. Optimization and scope of this method are reported.

Keywords: sp2 sp3; development sp2; hiv nnrti; cross coupling

Journal Title: Organic letters
Year Published: 2017

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