ChemInform Abstract: Synthesis of 3‐(Hetero)aryl Tetrahydropyrazolo[3,4‐c]pyridines by Suzuki—Miyaura Cross‐Coupling Methodology.

• DOI: 10.1002/chin.201508232
• Publication Date: 2015-02-05T10:16:57Z
• Authors: Paul D. Kemmitt; Kevin Blades; Matthew R. Box; Stephanie Dickinson; Gillian M. Lamont; Katrina Madden; William McCoull; Jason Williams
• Keywords: Molecular Structure; Pyridines; Benzyl Compounds; Pyrazoles; Esters; 01 natural sciences; Catalysis; Palladium; 0104 chemical sciences

A new synthetic route to 3-(heteroaryl) tetrahydropyrazolo[3,4-c]pyridines has been developed that uses the Suzuki-Miyaura 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.