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. 2017 Oct 10;22(10):1688.
doi: 10.3390/molecules22101688.

Synthesis of 11C-Labelled Ureas by Palladium(II)-Mediated Oxidative Carbonylation

Sara Roslin  1 , Peter Brandt  2 , Patrik Nordeman  3 , Mats Larhed  4 , Luke R Odell  5 , Jonas Eriksson  6
Affiliations

Synthesis of 11C-Labelled Ureas by Palladium(II)-Mediated Oxidative Carbonylation

Sara Roslin et al. Molecules. .

Abstract

Positron emission tomography is an imaging technique with applications in clinical settings as well as in basic research for the study of biological processes. A PET tracer, a biologically active molecule where a positron-emitting radioisotope such as carbon-11 has been incorporated, is used for the studies. Development of robust methods for incorporation of the radioisotope is therefore of the utmost importance. The urea functional group is present in many biologically active compounds and is thus an attractive target for incorporation of carbon-11 in the form of [11C]carbon monoxide. Starting with amines and [11C]carbon monoxide, both symmetrical and unsymmetrical 11C-labelled ureas were synthesised via a palladium(II)-mediated oxidative carbonylation and obtained in decay-corrected radiochemical yields up to 65%. The added advantage of using [11C]carbon monoxide was shown by the molar activity obtained for an inhibitor of soluble epoxide hydrolase (247 GBq/μmol-319 GBq/μmol). DFT calculations were found to support a reaction mechanism proceeding through an 11C-labelled isocyanate intermediate.

Keywords: 11C-labelling; carbon monoxide; carbon-11; carbonylation; positron emission tomography; urea.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Biologically active ureas.
Scheme 1
Scheme 1
Hypothetical reaction paths for 11C-labelled urea formation.
Scheme 2
Scheme 2
Calculated free energies (kcal/mol) of intermediates along path A in Scheme 1 showing that the path is energetically feasible.
See this image and copyright information in PMC

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