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Palladium‐mediated oxidative carbonylation reactions for the synthesis of 11 C‐radiolabelled ureas
Author(s) -
Kealey Steven,
Husbands Stephen M.,
Bennacef Idriss,
Gee Antony D.,
Passchier Jan
Publication year - 2014
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3151
Subject(s) - chemistry , carbonylation , palladium , amine gas treating , carbon monoxide , medicinal chemistry , reactivity (psychology) , oxidative addition , organic chemistry , catalysis , medicine , alternative medicine , pathology
Palladium(II)‐mediated oxidative carbonylation reactions have been used to synthesize 11 C‐radiolabelled ureas via the coupling of amines with [ 11 C]carbon monoxide, in a one‐pot process. Following trapping of 11 CO in a solution of copper(I) tris(3,5‐dimethylpyrazolyl)borate, homocoupling reactions of primary aliphatic amines proceed in the presence of Pd(PPh 3 ) 2 Cl 2 to give the corresponding N , N ‐disubstituted [ 11 C]ureas. Secondary amines do not produce the corresponding N , N , N , N ‐tetrasubsituted [ 11 C]ureas under these conditions. This difference in reactivity allows for the formation of unsymmetrical N , N ’, N ’‐trisubstituted [ 11 C]ureas using a mixture of a primary amine and a reactive secondary amine. The potential use of this method in positron emission tomography (PET) was demonstrated by the synthesis of the M1 muscarinic acetylcholine receptor radiotracer, [ 11 C‐ carbonyl ]GSK1034702.