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Molecules 2017, 22(10), 1688; doi:10.3390/molecules22101688

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

1
Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, BMC, Uppsala University, Box 574, SE-751 23 Uppsala, Sweden
2
Science for Life Laboratory, Department of Medicinal Chemistry, BMC, Uppsala University, Box 574, SE-751 23 Uppsala, Sweden
*
Author to whom correspondence should be addressed.
Received: 25 September 2017 / Revised: 4 October 2017 / Accepted: 4 October 2017 / Published: 10 October 2017
(This article belongs to the Special Issue Current Aspects of Radiopharmaceutical Chemistry)
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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. View Full-Text
Keywords: carbon-11; 11C-labelling; urea; carbonylation; positron emission tomography; carbon monoxide carbon-11; 11C-labelling; urea; carbonylation; positron emission tomography; carbon monoxide
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MDPI and ACS Style

Roslin, S.; Brandt, P.; Nordeman, P.; Larhed, M.; Odell, L.R.; Eriksson, J. Synthesis of 11C-Labelled Ureas by Palladium(II)-Mediated Oxidative Carbonylation. Molecules 2017, 22, 1688.

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