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Development of an Efficient Pd-Catalyzed Coupling Process for Axitinib
The manufacturing process of axitinib (1) involves two Pd-catalyzed coupling reactions, a Migita coupling and a Heck reaction. Optimization of both of these pivotal bond-formation steps is discussed
Development of nonproprietary phosphine ligands for the Pd-catalyzed amination reaction
Abstract A new family of pyrazole and bi-pyrazole phosphine ligands are reported that perform efficiently in the Pd-catalyzed amination reaction. Of the ligands screened, ligand 1 emerged as the most
Streamlined Synthesis of the Bippyphos Family of Ligands and Cross-Coupling Applications
We describe the efficient preparation of Bippyphos, 1. The key precursor to Bippyphos, 5, was prepared via a one-pot bromination of diketone 2 followed by alkylation with pyrazole and condensation
Palladium-catalyzed synthesis of N-aryloxazolidinones from aryl chlorides.
TLDR
The coupling reaction can be used to prepare enantiopure N-aryl beta-amino alcohols and allow the use of cheaper aryl chlorides containing functionalities such as enolizable ketones, amides, etc., which would be incompatible with other coupling methods.
Cu-catalyzed N-arylation of oxazolidinones: an efficient synthesis of the kappa-opioid receptor Agonist CJ-15161.
TLDR
An efficient method for intermolecular N-arylation of oxazolidinones using catalytic copper in the presence of a bidentate ligand is reported and a short, scalable synthesis of CJ-15,161 is reported.
A practical, efficient, and rapid method for the oxidation of electron deficient pyridines using trifluoroacetic anhydride and hydrogen peroxide–urea complex
Abstract A general method for the oxidation of electron-poor pyridines to their N-oxides using UHP and TFAA in either CH2Cl2 or CH3CN was developed. The methodology proved to tolerate a number of
Process Research and Development of an NK-1 Receptor Antagonist. Enantioselective Trifluoromethyl Addition to a Ketone in the Preparation of a Chiral Isochroman
CJ-17,493 (4) is a chiral NK-1 receptor antagonist. It was first prepared through a diastereoselective crystallization, then through chiral chromatography of a key intermediate, and ultimately via
Synthesis of Filibuvir. Part I. Diastereoselective Preparation of a β-Hydroxy Alkynyl Oxazolidinone and Conversion to a 6,6-Disubstituted 2H-Pyranone
This is the first in a series of three papers describing the identification and development of a commercial synthesis of filibuvir (1). This contribution describes development of an Evans aldol
Preparation of a Corticotropin-Releasing Factor Antagonist by Nucleophilic Aromatic Substitution and Copper-Mediated Ether Formation†
Several synthetic approaches to a corticotropin-releasing factor (CRF) antagonist containing a tetrasubstituted pyridine were evaluated. In particular, nucleophilic aromatic substitutions on
Development of the Commercial Route for the Manufacture of a 5-Lipoxygenase Inhibitor PF-04191834
A de novo three-step-one-pot process for the formation of PF-04191834 was developed. This methodology employed inexpensive, odorless, and readily available commodity chemical
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