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Synthesis of Two Fluoro Analogues of the Nicotinic Acetylcholine Receptor Agonist UB-165

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journal contribution
posted on 20.02.2003, 00:00 by Andrew Sutherland, Timothy Gallagher, Christopher G. V. Sharples, Susan Wonnacott
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 α4β2 and α7 nicotinic receptors.