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J Org Chem. 2011 Mar 4;76(5):1436-9. doi: 10.1021/jo1018574. Epub 2011 Feb 1.

Preparative scale synthesis of the biaryl core of anacetrapib via a ruthenium-catalyzed direct arylation reaction: unexpected effect of solvent impurity on the arylation reaction.

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1
Department of Process Research, Merck Frosst Canada, Kirkland, Quebec, Canada. stephane_ouellet@merck.com

Abstract

In this report, we disclose our findings regarding the remarkable effect of a low-level impurity found in the solvent used for a ruthenium-catalyzed direct arylation reaction. This discovery allowed for the development of a robust and high-yield arylation protocol that was demonstrated on a multikilogram scale using carboxylate as the cocatalyst. Finally, a practical, scalable, and chromatography-free synthesis of the biaryl core of Anacetrapib is described.

PMID:
21284400
DOI:
10.1021/jo1018574
[Indexed for MEDLINE]
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