An Efficient and Cost-Effective Synthesis of 2-Phenyl-3-aminopyridine

The synthesis of 2-phenyl-3-aminopyridine, a key intermediate in the preparation of 2-phenyl-3-aminopiperidine, from 2-chloro-3-aminopyridine is described using an imine as a protecting group for an aminopyridine. The in situ protection of 2-chloro-3-aminopyridine with benzaldehyde followed by Suzuk...

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Bibliographic Details
Published inOrganic process research & development Vol. 5; no. 3; pp. 254 - 256
Main Authors Caron, Stéphane, Massett, Steve S., Bogle, David E., Castaldi, Michael J., Braish, Tamim F.
Format Journal Article
LanguageEnglish
Published American Chemical Society 01.05.2001
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Summary:The synthesis of 2-phenyl-3-aminopyridine, a key intermediate in the preparation of 2-phenyl-3-aminopiperidine, from 2-chloro-3-aminopyridine is described using an imine as a protecting group for an aminopyridine. The in situ protection of 2-chloro-3-aminopyridine with benzaldehyde followed by Suzuki coupling with phenylboronic acid and subsequent acid hydrolysis provided the titled compound in a single, high-yielding step from inexpensive and commercially available starting materials.
ISSN:1083-6160
1520-586X
DOI:10.1021/op000227e