Synthesis of 3-(Hetero)aryl Tetrahydropyrazolo[3,4-c]pyridines by Suzuki鈥揗iyaura Cross-Coupling Methodology

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• 作者：Paul D. Kemmitt ; Kevin Blades ; Matthew R. Box ; Stephanie Dickinson ; Gillian M. Lamont ; Katrina Madden ; William McCoull ; Jason Williams
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：August 15, 2014
• 年：2014
• 卷：79
• 期：16
• 页码：7682-7688
• 全文大小：328K
• ISSN：1520-6904

文摘

A new synthetic route to 3-(heteroaryl) tetrahydropyrazolo[3,4-c]pyridines has been developed that uses the Suzuki鈥揗iyaura cross-coupling of a triflate 6 with (hetero)aryl boronic acids or esters. Using Pd(OAc)₂ and XPhos or an XPhos precatalyst, a diverse range of substituents at the C3 position of the tetrahydropyrazolo[3,4-c]pyridine skeleton were prepared. The use of pivaloyloxymethyl and benzyl protection also offers the potential to differentially functionalize the pyrazole and tetrahydropyridine nitrogens.