Transition metal-catalyzed couplings in process chemistry : case studies from the pharmaceutical industry /: case studies from the pharmaceutical industry. (2013)

• Record Type: Book
• Further Information: Note: Edited by Javier Magano, Joshua R. Dunetz.
• Editors: Magano, Javier; Dunetz, Joshua R
• Contents: FOREWORD 1; FOREWORD 2; FOREWORD 3; ; INTRODUCTION; ; COPPER-CATALYZED COUPLING FOR A GREEN PROCESS; Introduction; Synthesis of Amino Acid 14; Copper-Catalyzed Cyclization; Sustainability; Summary; ; EXPERIENCES WITH NEGISHI COUPLINGS ON TECHNICAL SCALE IN EARLY DEVELOPMENT; Introduction; Synthesis of LBT613 via Pd-Catalyzed Negishi Coupling; Elaboration of a Negishi Coupling in the Synthesis of PDE472; Ni-Catalyzed Negishi Coupling with Catalytic Amounts of ZnCl2; Conclusions; ; DEVELOPING PALLADIUM-CATALYZED ARYLATIONS OF CARBONYL-ACTIVATED C -; H BONDS; Introduction; Suzuki Approach to Side Chain Installation; Arylation of Carbonyl-Activated C -; H Bonds; Pd Purging from API; Conclusions; ; DEVELOPMENT OF A PRACTICAL SYNTHESIS OF NAPHTHYRIDONE P38 MAP KINASE INHIBITOR MK-0913; Introduction; Medicinal Chemistry Approach to 1; Results and Discussion; Conclusions ; ; PRACTICAL SYNTHESIS OF A CATHEPSIN S INHIBITOR; Introduction; Synthetic Strategy; Syntheses of Building Blocks; Sonogashira Coupling and Initial Purification of 1; Salt Selection; Conclusions; ; C -; N COUPLING CHEMISTRY AS A MEANS TO ACHIEVE A COMPLICATED MOLECULAR ARCHITECTURE: THE AR-A2 CASE STORY; A Novel Chemical Entity; Evaluation of Synthetic Pathways: Finding the Best Route; Enabling C -; N Coupling by Defining the Reaction Space; From Synthesis to Process; Concluding Remarks; ; PROCESS DEVELOPMENT AND SCALE-UP OF PF-03941275, A NOVEL ANTIBIOTIC; Introduction; Medicinal Chemistry Synthesis of PF-03941275; Synthesis of 5-Bromo-2, 4-difluorobenzaldehyde (1); Synthesis of Amine 3; Miyaura Borylation Reaction; Suzuki -; Miyaura Coupling; Barbituric Acid Coupling; Chlorination and API Isolation; Conclusions; ; DEVELOPMENT OF A PRACTICAL NEGISHI COUPLING PROCESS FOR THE MANUFACTURING OF BILB 1941, AN HCV POLYMERASE INHIBITOR; Introduction and Background; Stille Coupling; Suzuki Coupling; Negishi Coupling; Comparison of Three Coupling Processes; ; APPLICATION OF A RHODIUM-CATALYZED, ASYMMETRIC 1, 4-ADDITION TO THE KILOGRAM-SCALE MANUFACTURE OF A PHARMACEUTICAL INTERMEDIATE; Introduction; Early Development; Process Optimization; Process Scale-up; Recent Developments; Conclusions; ; COPPER-CATALYZED C -; N COUPLING ON LARGE SCALE: AN INDUSTRIAL CASE STUDY; Introduction; Process Development of the C -; N Bond Formation; Choice of Catalytic System; Choice of Base: Inorganic Versus Organic; Choice of Solvent; Optimized Conditions for C -; N Bond Formation to 1; Purging Residual Copper from 1; Conclusions; ; DEVELOPMENT OF A HIGHLY EFFICIENT REGIO- AND STEREOSELECTIVE HECK REACTION FOR THE LARGE-SCALE MANUFACTURE OF AN A4B2 NNR AGONIST; Introduction; Process Optimization; Conclusions; ; COMMERCIAL DEVELOPMENT OF AXITINIB (AG-013736): OPTIMIZATION OF A CONVERGENT PD-CATALYZED COUPLING ASSEMBLY AND SOLID FORM CHALLENGES; Introduction; First-Generation Synthesis of Axitinib; Early Process Research and Development; Commercial Route Development; Conclusions; ; LARGE-SCALE SONOGASHIRA COUPLING FOR THE SYNTHESIS OF AN MGLUR5 NEGATIVE ALLOSTERIC MODULATOR; Introduction; Background; Process Development of the Sonogashira Coupling; Large-Scale Sonogashira Coupling and API Purification; Conclusions; ; PALLADIUM-CATALYZED BISALLYLATION OF ERYTHROMYCIN DERIVATIVES; Introduction; Discovery of 6, 11-O, O-Bisallylation of Erythromycin Derivatives; Process Development of 6, 11-O, O-Bisallylation of Erythromycin Derivatives; Discovery and Optimization of 3, 6-Bicyclolides; Conclusions; ; ROUTE SELECTION AND PROCESS DEVELOPMENT FOR THE VANILLOID RECEPTOR-1 ANTAGONIST AMG 517; Introduction; Retrosynthesis and Medicinal Chemistry Route; Optimization of Medicinal Chemistry Route; Identification of the Process Chemistry Route; Optimization of the Suzuki -; Miyaura Reaction; Postcampaign Improvements; Summary; ; TRANSITION METAL-CATALYZED COUPLING REACTIONS IN THE SYNTHESIS OF TARANABANT: FROM INCEPTION TO PILOT IMPLEMENTATION; Introduction; Development of Pd-Catalyzed Cyanations; Development of Pd-Catalyzed Amidation Reactions; Conclusions; ; RING-CLOSING METATHESIS IN THE LARGE-SCALE SYNTHESIS OF SB-462795; Background; The RCM Disconnection; The RCM of Diene 5; ; DEVELOPMENT OF MIGITA COUPLINGS FOR THE MANUFACTURE OF A 5-LIPOXYGENASE INHIBITOR; Introduction; Evaluation of the Sulfur Source for Initial Migita Coupling; Selection of Metal Catalyst and Coupling Partners; Development of a One-Pot, Two-Migita Coupling Process; Crystallization of 1 with Polymorph Control; Final Commercial Process on Multikilogram Scale; Conclusions; ; PREPARATION OF 4-ALLYLISOINDOLINE VIA A KUMADA COUPLING WITH ALLYLMAGNESIUM CHLORIDE; Introduction; Kumada Coupling of 4-Bromoisoindoline; Workup; Isolation; Conclusions; ; MICROWAVE HEATING AND CONTINUOUS-FLOW PROCESSING AS TOOLS FOR METAL-CATALYZED COUPLINGS: PALLADIUM-CATALYZED SUZUKI -; MIYAURA, HECK, AND ALKOXYCARBONYLATION REACTIONS; Introduction; Coupling Reactions Performed Using Microwave Heating or Continuous-Flow Processing; Conclusions; ; APPLYING THE HYDROPHOBIC EFFECT TO TRANSITION METAL-CATALYZED COUPLINGS IN WATER AT ROOM TEMPERATURE; Introduction: the Hydrophobic Effect under Homogeneous and Heterogeneous Conditions; Micellar Catalysis Using Designer Surfactants; First Generation: PTS; Heck Couplings in Water at rt; Olefin Metathesis Going Green; Adding Ammonia Equivalents onto Aromatic and Heteroaromatic Rings; Couplings with Moisture-Sensitive Organometallics in Water; A New, Third-Generation Surfactant: 'Nok'; Summary, Conclusions, and a Look Forward; ; LARGE-SCALE APPLICATIONS OF TRANSITION METAL REMOVAL TECHNIQUES IN THE MANUFACTURE OF PHARMACEUTICALS; Introduction; Methods that Precipitate or Capture/Extract the Metal while Maintaining the Coupling Product in Solution; Methods that Precipitate the Coupling Product while Purging the Metal to the Filtrates; Miscellaneous Methods; Other Methods for Metal Removal; Conclusions; ; INDEX;
• Publisher Details: Place of publication not identified : Wiley-VCH
• Publication Date: 2013
• Extent: 1 online resource (401 pages)
• Subjects: 660.2995; Transition metal catalysts; Drug development; Drug development -- Case studies
• Languages: English
• ISBNs: 9783527658923
• Access Rights: Legal Deposit; Only available on premises controlled by the deposit library and to one user at any one time; The Legal Deposit Libraries (Non-Print Works) Regulations (UK).
• Access Usage: Restricted: Printing from this resource is governed by The Legal Deposit Libraries (Non-Print Works) Regulations (UK) and UK copyright law currently in force.