Synlett 2019; 30(15): 1776-1781
DOI: 10.1055/s-0037-1611909
letter
© Georg Thieme Verlag Stuttgart · New York

Warming Up to Oxazole: Noncryogenic Oxazole Metalation and Negishi Coupling Development

Michael J. Geier
,
Xiaotian Wang
,
Luke D. Humphreys
,
Selcuk Calimsiz
,
Mark E. Scott
Department of Process Chemistry, Gilead Alberta ULC, 1021 Hayter Road NW, Edmonton, Alberta T6S 1A1, Canada   eMail: mark.scott@gilead.com
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Publikationsverlauf

Received: 14. Mai 2019

Accepted after revision: 27. Juli 2019

Publikationsdatum:
19. August 2019 (online)


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Abstract

This report details the development of several suitable noncryogenic metalation conditions for the synthesis of oxazole zincate. Subsequent rounds of high-throughput catalyst screening ultimately led to the identification of several suitable Pd sources that can be used for the Negishi coupling of unsubstituted oxazole. The scope and generality for one of the reported conditions is also presented.

Supporting Information