Synthetic utility of 4-bromo-2,3,5,6-tetrafluoropyridine |
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Authors: | John A Christopher Laura Brophy Sean M Lynn David D Miller Lisa A Sloan Graham Sandford |
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Institution: | aGlaxoSmithKline R&D, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, UK bDepartment of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK |
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Abstract: | The regiochemistry of nucleophilic substitution of 4-bromo-2,3,5,6-tetrafluoropyridine has been investigated. Efficient, regioselective reactions occur with alkylamine, benzylamine and alkoxide nucleophiles, yielding products where substitution occurs ortho to the ring nitrogen. The resulting 2-substituted-4-bromo-3,5,6-trifluoropyridines can be functionalised further, either by a second regioselective nucleophilic displacement or palladium catalysed elaboration at the 4-position. Reactions with aromatic N-nucleophiles yield mixtures of ortho- and para-substituted products. |
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Keywords: | Heterocyclic Scaffold Perfluoroheterocycle 4-Bromo-2 3 5 6-tetrafluoropyridine Suzuki reaction Nucleophilic aromatic substitution |
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