Palladium-mediated 11C-carbonylations using aryl halides and cyanamide. 2017

P Nordeman, and S Y Chow, and A F Odell, and G Antoni, and L R Odell
Preclinical PET Platform Chemistry, Department of Medicinal Chemistry, Uppsala University, Sweden.

A robust and high-yielding radiochemical synthesis of 11C-N-cyanobenzamides using a palladium-mediated aminocarbonylation with 11C-CO, aryl halides and cyanamide is described. The bidentate ligand 1,1'-bis(diphenylphosphino)ferrocene provided 11C-N-cyanobenzamides from aryl-iodides, bromides, triflates and even chlorides in 28-79% radiochemical yield after semi-preparative HPLC. To further highlight the utility of this method, novel 11C-N-cyanobenzamide analogs of flufenamic acid, meflanamic acid, dazoxiben and tamibarotene were synthesized in 34-71% radiochemical yields.

UI MeSH Term Description Entries
D010165 Palladium A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.
D003484 Cyanamide A cyanide compound which has been used as a fertilizer, defoliant and in many manufacturing processes. It often occurs as the calcium salt, sometimes also referred to as cyanamide. The citrated calcium salt is used in the treatment of alcoholism. Calcium Carbimide,Calcium Cyanamide,Citrated Calcium Cyanamide,Abstem,Carbimide,Colme,Cyanamide, Calcium (1:1) Salt,Cyanamide, Calcium (2:1) Salt,Cyanamide, Calcium Salt,Temposil,Calcium Cyanamide, Citrated,Calcium Salt Cyanamide,Carbimide, Calcium,Cyanamide, Calcium,Cyanamide, Citrated Calcium
D006846 Hydrocarbons, Halogenated Hydrocarbon compounds with one or more HYDROGEN atoms substituted with HALOGENS. Halogenated Hydrocarbons
D001549 Benzamides BENZOIC ACID amides.
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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