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Synthesis of substituted [ 11 C]ureas and [ 11 C]sulphonylureas by Rh(I)‐mediated carbonylation
Author(s) -
Åberg Ola,
Långström Bengt
Publication year - 2011
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.1803
Subject(s) - chemistry , carbon monoxide , carbonylation , urea , phosgene , moiety , amine gas treating , carbon 14 , azide , medicinal chemistry , rhodium , organic chemistry , catalysis , physics , quantum mechanics
The urea moiety is present in many biologically active compounds and thus an attractive target for 11 C‐labelling. To extend the scope of the rhodium(I)‐mediated carbonylative cross‐coupling reaction between an azide and an amine and investigate its tolerance for functional groups, we have synthesized eight ureas and two sulphonylureas that were 11 C‐labelled in the carbonyl position. The decay‐corrected analytical radiochemical yields were in the range of 14–96% (from [ 11 C]carbon monoxide). For example: starting from 1.33 GBq [ 11 C]carbon monoxide, 0.237 GBq (66%) of the cytotoxic sulphonylurea [ 11 C]LY‐181984 11 was isolated within 60 min from end of bombardment. The mild reaction conditions and generality regarding functional groups of this method make it an attractive alternative to the [ 11 C]phosgene method for the synthesis of 11 C‐labelled ureas. Copyright © 2010 John Wiley & Sons, Ltd.