The discovery, development, and optimization of a complex copper-mediated Ullmann-Goldberg-Buchwald coupling of 7-bromoazaindole 1 and 3-methyl-1,2,4-triazole (2) will be described. This Ullmann-Goldberg-Buchwald coupling enabled the preparation of the antepenultimate intermediate 3 in the synthesis of a novel antiretroviral. Several key challenges associated with developing a commercial process will be discussed including reaction development, a copper remediation strategy and identifying a suitable crystalline form of 3 to facilitate isolation on large scale.

Development of a commercial viable, highly regioselective copper catalyzed N-arylation of 3-methyl-1,2,4-triazole

254th National Meeting (2017)

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