title: Synthesis of 3-(hetero)aryl tetrahydropyrazolo[3,4-c]pyridines by Suzuki-Miyaura cross-coupling methodology.
abstract: 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.
authors: AstraZeneca Oncology Innovative Medicines , Mereside, Alderley Park, Macclesfield Cheshire, SK10 4TG, United Kingdom.
authors: Paul D
authors: PD
authors: Kemmitt
authors: Kevin
authors: K
authors: Blades
authors: Matthew R
authors: MR
authors: Box
authors: Stephanie
authors: S
authors: Dickinson
authors: Gillian M
authors: GM
authors: Lamont
authors: Katrina
authors: K
authors: Madden
authors: William
authors: W
authors: McCoull
authors: Jason
authors: J
authors: Williams
mesh_terms: D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001593:Benzyl Compounds; D004952:Esters; D011720:Pyrazoles; D011725:Pyridines; D010165:Palladium