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J Org Chem. 2003 Mar 21;68(6):2475-8.

Synthesis of two fluoro analogues of the nicotinic acetylcholine receptor agonist UB-165.

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  • 1School of Chemistry, University of Bristol, Bristol BS8 1TS, United Kingdom.


Two racemic fluoropyridine analogues 4 and 5 of the potent nicotinic agonist UB-165 have been synthesized. Halogenated pyridines 7 and 12 provided the organometallic reagents needed for the Negishi and Suzuki coupling reactions used for the preparation of 4 and 5, and the N-vinyloxycarbonyl protecting group of 8 and 15 was cleaved using a novel trifluoroacetic acid-mediated deprotection protocol. Analogue 4 retained high binding affinity at rat brain alpha4beta2 and alpha7 nicotinic receptors.

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