Premium
One‐Pot Synthesis of 11 C‐Labelled Primary Benzamides via Intermediate [ 11 C]Aroyl Dimethylaminopyridinium Salts
Author(s) -
Ferrat Mélodie,
Dahl Kenneth,
Schou Magnus
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100544
Subject(s) - chemistry , benzamide , electrophile , aryl , primary (astronomy) , halide , veliparib , medicinal chemistry , combinatorial chemistry , radiochemistry , organic chemistry , catalysis , polymerase , poly adp ribose polymerase , alkyl , physics , enzyme , astronomy
Electrophilic 11 C‐labelled aroyl dimethylaminopyridinium salts, obtained by carbonylative cross‐coupling of aryl halides with [ 11 C]carbon monoxide, were prepared for the first time and shown to be valuable intermediates in the synthesis of primary [ 11 C]benzamides. The methodology furnished a set of benzamide model compounds, including the two poly (ADP‐ribose) polymerase (PARP) inhibitors niraparib and veliparib, in moderate to excellent radiochemical yields. In addition to providing a convenient and practical route to primary [ 11 C]benzamides, the current method paves the way for future application of [ 11 C]aroyl dimethylaminopyridinium halide salts in positron emission tomography (PET) tracer synthesis.