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Journal of Medicinal Chemistry

Journal of Medicinal Chemistry

IF: 6.8
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End-to-End Automated Synthesis of C(sp3)-Enriched Drug-like Molecules via Negishi Coupling and Novel, Automated Liquid–Liquid Extraction

Published:15 December 2022 DOI: 10.1021/acs.jmedchem.2c01646
Irini Abdiaj*, Santiago Ca?ellas, Alejandro Dieguez, Maria Lourdes Linares, Brenda Pijper, Alberto Fontana, Raquel Rodriguez, Andres Trabanco, Eduardo Palao and Jesus Alcázar*, 

Abstract

Herein, we report an end-to-end process including synthesis, work-up, purification, and post-purification with minimal human intervention using Negishi coupling as a key transformation to increase Fsp3 in bioactive molecules. The main advantages of this protocol are twofold. First, the automated sequential generation of organozinc reagents from readily available alkyl halides offers a large diversity of alkyl groups to functionalize (hetero)aryl halide scaffolds via Pd-catalyzed Negishi coupling in continuous flow. Second, a fully automated liquid–liquid extraction has been developed and successfully applied for unattended operations. The workflow was completed with mass-triggered preparative high-performance liquid chromatography HPLC, providing an efficient production line of compounds with enriched sp3 character and better drug-like properties. The modular nature allows a smooth adaptation to a wide variety of synthetic methods and protocols and makes it applicable to any medchem laboratory.

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