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Transition metal-catalyzed couplings in process chemistry : case studies from the pharmaceutical industry /
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...
| Clasificación: | Libro Electrónico |
|---|---|
| Otros Autores: | , |
| Formato: | Electrónico eBook |
| Idioma: | Inglés |
| Publicado: |
Weinheim, Germany :
Wiley-VCH,
Ã2013.
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| Edición: | First edition. |
| Temas: | |
| Acceso en línea: | Texto completo |
Tabla de Contenidos:
- 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.