A silver triflate promoted cyclization to produce substituted oxazoles in a single step is presented as an alternative to a low yielding thermal cyclization reaction that generated complex product mixtures.  Silver activation of the bromide toward nucleophilic attack by the amide followed by cyclization and dehydration is the likely mechanism.  The new process delivered kilogram quantities of a key oxazole intermediate in high yield and purity.

Development of a large-scale synthesis of tri-substituted oxazoles via a novel silver triflate mediated cyclization

244th National Meeting (2012)

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