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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Veröffentlicht in:Organic process research & development 2001-05, Vol.5 (3), p.254-256
Hauptverfasser: Caron, Stéphane, Massett, Steve S., Bogle, David E., Castaldi, Michael J., Braish, Tamim F.
Format: Artikel
Sprache:eng
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Zusammenfassung: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