A General Kilogram Scale Protocol for Suzuki–Miyaura Cross-Coupling in Water with TPGS-750-M Surfactant
Michaël Parmentier, Mona Wagner, Regina Wickendick, Markus Baenziger, Audrey Langlois, Fabrice Gallou
Abstract
The development of a kilogram scale protocol for a Suzuki–Miyaura cross-coupling step toward the synthesis of the drug candidate LSZ102 is described. Particularly, the use of the surfactant TPGS-750-M in water as a medium for the transformation and its impact on the selectivity and quality are reported. Minimization of typical impurities generated during the cross-coupling (e.g., dehalogenation) has been in focus during our study. The environmental and cost impacts using such a process are also discussed.
Topics & Concepts
Pulmonary surfactantChemistryKilogramCoupling (piping)HalogenationCombinatorial chemistryChromatographyMaterials scienceOrganic chemistryBody weightMedicineBiochemistryMetallurgyInternal medicineCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis TechniquesChemistry and Chemical Engineering