Abstract
A Cu-mediated ortho-C-H radiofluorination of aromatic carboxylic acids that are protected as 8-aminoquinoline benzamides is described. The method uses K18 F and is compatible with a wide range of functional groups. The reaction is showcased in the high specific activity automated synthesis of the RARβ2 agonist [18 F]AC261066.
Keywords:
C−H fluorination; C−H functionalization; PET radiochemistry; fluorine-18; late-stage fluorination.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Aminoquinolines / chemical synthesis
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Aminoquinolines / chemistry*
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Benzamides / chemical synthesis
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Benzamides / chemistry*
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Benzoates / chemical synthesis*
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Benzoates / chemistry
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Copper / chemistry*
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Fluorine Radioisotopes / chemistry*
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Halogenation
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Humans
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Radiopharmaceuticals / chemical synthesis
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Radiopharmaceuticals / chemistry
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Receptors, Retinoic Acid / agonists
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Thiazoles / chemical synthesis*
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Thiazoles / chemistry
Substances
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4-(4-(2-(n-butoxy)ethoxy)-5-methylthiazol-2-yl)-2-fluorobenzoic acid
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Aminoquinolines
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Benzamides
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Benzoates
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Fluorine Radioisotopes
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Radiopharmaceuticals
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Receptors, Retinoic Acid
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Thiazoles
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retinoic acid receptor beta
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Copper
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Fluorine-18
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8-aminoquinoline