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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• 作者：Ste虂phane G. Ouellet ; Ame虂lie Roy ; Carmela Molinaro ; Re虂my Angelaud ; Jean-Franc抬ois Marcoux ; Paul D. O鈥橲hea ; Ian W. Davies
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：March 4, 2011
• 年：2011
• 卷：76
• 期：5
• 页码：1436-1439
• 全文大小：768K
• 年卷期：v.76,no.5(March 4, 2011)
• ISSN：1520-6904

文摘

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.