3 years ago

Synthesis of N-Substituted 3-Amino-4-halopyridines: A Sequential Boc-Removal/Reductive Amination Mediated by Brønsted and Lewis Acids

Synthesis of N-Substituted
3-Amino-4-halopyridines: A Sequential Boc-Removal/Reductive
Amination Mediated by Brønsted and Lewis Acids
John D. Chisholm, Daniel A. Clark, Alexandre D.C. Dixon, Christopher A. Wilhelmsen
N-Substituted 3-amino-4-halopyridines are valuable synthetic intermediates, as they readily provide access to imidazopyridines and similar heterocyclic systems. The direct synthesis of N-substituted 3-amino-4-halopyridines is problematic, as reductive aminations and base-promoted alkylations are difficult in these systems. A high yielding deprotection/alkylation protocol mediated by trifluoroacetic acid and trimethylsilyl trifluoromethanesulfonate is described, providing access to a wide scope of N-substituted 3-amino-4-halopyridines. This protocol furnishes many reaction products in high purity without chromatography. Similar reductive amination conditions were also established for deactivated anilines.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02966

DOI: 10.1021/acs.joc.7b02966

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