A Buchwald-Hartwig Protocol to Enable Rapid Linker Exploration of Cereblon E3-Ligase PROTACs*

Chemistry. 2020 Dec 15;26(70):16818-16823. doi: 10.1002/chem.202003137. Epub 2020 Nov 3.

Abstract

A palladium-catalysed Buchwald-Hartwig amination for lenalidomide-derived aryl bromides was optimised using high throughput experimentation (HTE). The substrate scope of the optimised conditions was evaluated for a range of alkyl- and aryl- amines and functionalised aryl bromides. The methodology allows access to new cereblon-based bifunctional proteolysis targeting chimeras with a reduced step count and improved yields.

Keywords: PEPPSI; PROTAC; amination; cereblon; drug discovery.

MeSH terms

  • Amination
  • Amines / chemistry*
  • Bromides / chemistry*
  • Lenalidomide / chemistry*
  • Ligands
  • Proteolysis / drug effects*
  • Ubiquitin-Protein Ligases / metabolism

Substances

  • Amines
  • Bromides
  • Ligands
  • Ubiquitin-Protein Ligases
  • Lenalidomide