Title Transition metal-catalyzed couplings in process chemistry : case studies from the pharmaceutical industry / edited by Javier Magano and Joshua R. Dunetz

Edition First edition Published Weinheim, Germany : Wiley-VCH, ©2013

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Description 1 online resource (xxxvii, 368 pages) Contents Related Titles; Title Page; Copyright; Foreword 1; Foreword 2; Foreword 3; List of Contributors; Introduction; List of Abbreviations; Chapter 1: Copper-Catalyzed Coupling for a Green Process; 1.1 Introduction; 1.2 Synthesis of Amino Acid 14; 1.3 Copper-Catalyzed Cyclization; 1.4 Sustainability; 1.5 Summary; Acknowledgments; References; Chapter 2: Experiences with Negishi Couplings on Technical Scale in Early Development; 2.1 Introduction; 2.2 Synthesis of LBT613 via Pd-Catalyzed Negishi Coupling; 2.3 Elaboration of a Negishi Coupling in the Synthesis of PDE472 2.4 Ni-Catalyzed Negishi Coupling with Catalytic Amounts of ZnCl22.5 Conclusions; References; Chapter 3: Developing Palladium-Catalyzed Arylations of Carbonyl-Activated C-H Bonds; 3.1 Introduction; 3.2 Suzuki Approach to Side Chain Installation; 3.3 Arylation of Carbonyl-Activated C-H Bonds; 3.4 Pd Purging from API; 3.5 Conclusions; References; Chapter 4: Development of a Practical Synthesis of Naphthyridone p38 MAP Kinase Inhibitor MK-0913; 4.1 Introduction; 4.2 Medicinal Chemistry Approach to 1; 4.3 Results and Discussion; 4.4 Conclusions; References Chapter 5: Practical Synthesis of a Cathepsin S Inhibitor5.1 Introduction; 5.2 Synthetic Strategy; 5.3 Syntheses of Building Blocks; 5.4 Sonogashira Coupling and Initial Purification of 1; 5.5 Salt Selection; 5.6 Conclusions; Acknowledgments; References; Chapter 6: C-N Coupling Chemistry as a Means to Achieve a Complicated Molecular Architecture: the AR-A2 Case Story; 6.1 A Novel Chemical Entity; 6.2 Evaluation of Synthetic Pathways: Finding the Best Route; 6.3 Enabling C-N Coupling by Defining the Reaction Space; 6.4 From Synthesis to Process; 6.5 Concluding Remarks; References Chapter 7: Process Development and Scale-up of PF-03941275, a Novel Antibiotic7.1 Introduction; 7.2 Medicinal Chemistry Synthesis of PF-03941275; 7.3 Synthesis of 5-Bromo-2,4-difluorobenzaldehyde (1); 7.4 Synthesis of Amine 3; 7.5 Miyaura Borylation Reaction; 7.6 Suzuki-Miyaura Coupling; 7.7 Barbituric Acid Coupling; 7.8 Chlorination and API Isolation; 7.9 Conclusions; Acknowledgments; References; Chapter 8: Development of a Practical Negishi Coupling Process for the Manufacturing of BILB 1941, an HCV Polymerase Inhibitor; 8.1 Introduction and Background; 8.2 Stille Coupling 8.3 Suzuki Coupling8.4 Negishi Coupling; 8.5 Comparison of Three Coupling Processes; References; Chapter 9: Application of a Rhodium-Catalyzed, Asymmetric 1,4-Addition to the Kilogram-Scale Manufacture of a Pharmaceutical Intermediate; 9.1 Introduction; 9.2 Early Development; 9.3 Process Optimization; 9.4 Process Scale-up; 9.5 Recent Developments; 9.6 Conclusions; Acknowledgments; References; Chapter 10: Copper-Catalyzed C-N Coupling on Large Scale: An Industrial Case Study; 10.1 Introduction; 10.2 Process Development of the C-N Bond Formation; 10.3 Choice of Catalytic System Summary This one-stop reference source is the first on this new and exciting technology to focus on case studies of large-scale industrial applications, presenting the information and facts that are otherwise hard to find in the current literature. Authors from Pfizer, Merck, DSM, Novartis, Amgen, and Astra Zeneca, among others, use case studies to showcase project evolution from inception to early and late development, including commercial routes where applicable. Each case study details at least one transition metal-catalyzed cross-coupling step, with special emphasis on lessons learned fro Notes Edition statement from running title area Bibliography Includes bibliographical references and index Notes Print version record Subject Catalysis. Pharmaceutical industry Catalysis Drug Industry SCIENCE -- Chemistry -- Physical & Theoretical. Catalysis Pharmaceutical industry Form Electronic book Author Magano, Javier Dunetz, Joshua R LC no. 2013372029 ISBN 9783527658909 3527658904 9783527658930 3527658939 1299712681 9781299712683 9783527332793 3527332790

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