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Accelerated Synthesis of Bicyclo[1.1.1]pentylamines: A High-Throughput Approach.

Maialen AlonsoSantiago CañellasFrancisca DelgadoMarta SerranoAlejandro Diéguez-VázquezJosé Enrique Gómez
Published in: Organic letters (2023)
Strained bicyclic substructures such as bicyclo[1.1.1]pentylamines (BCPAs) are increasingly targeted in medicinal chemistry as arylamine bioisosteres. Here, we leverage high-throughput automated synthesis to rapidly develop library-amenable reaction conditions and maximize design space to expand access to BCPAs. This new protocol relies on a copper-mediated C-N coupling approach and uses accessible and bench-stable iodo-BCP building blocks. Its applicability has been exemplified by incorporating BCPs in drug-like compounds, providing straightforward access to a library of valuable aniline-like isosteres.
Keyphrases
  • high throughput
  • single cell
  • randomized controlled trial
  • emergency department
  • drug induced
  • electronic health record