Transition Metal-Catalyzed Couplings in Process Chemistry: Case Studies From the Pharmaceutical Industry

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9783527332793: Transition Metal-Catalyzed Couplings in Process Chemistry: Case Studies From the Pharmaceutical Industry

Transition metal-catalyzed coupling reactions have a rich history that led to the awarding of the 2010 Nobel Prize in Chemistry to Professors Suzuki, Heck, and Negishi for their pioneering contributions to the field. The coming of age of this active area of research is showcased in this
book through case studies in which process chemists from the pharmaceutical industry share their personal experiences developing their own transition metal-catalyzed couplings for the large-scale manufacture of active pharmaceutical ingredients.

Authors from Pfizer, Merck, Boehringer-Ingelheim, Novartis, Amgen, GSK, AstraZeneca, and other companies describe the evolution of robust coupling processes from inception through early and late development, including commercial routes where applicable. This book covers a wide range of coupling transformations while capturing the lessons learned from each process. Every case study details the optimization of at least one transition metal-catalyzed coupling while elaborating on issues such as design of experiments, scalability and throughput, product purification, process safety, and waste management. The important issue of metal removal and the different technologies available to accomplish this goal are also addressed. Finally, a section covers novel technologies for cross-coupling with high potential for future applications on a large scale, such as microwave and flow chemistry as well as green cross-couplings performed in water.

With Forewords by Stephen L. Buchwald, Massachusetts Institute of Technology, Trevor Laird, Editor of Organic Process Research and Development and Neal G. Anderson, Anderson's Process Solutions LLC.

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About the Author:

Javier Magano was born in Madrid, Spain. He received a B.S. in organic chemistry from Complutense University in Madrid in 1987 and a M.Sc. degree in chemistry from the University of Michigan in 1990. After working for the oil industry in Spain for several years, he obtained a M.Sc. degree in rubber and polymer science at the Center for Advanced Scientific Research in Madrid. After moving back to the United States, he joined the early process chemistry group at Pfizer in 1998 in Ann Arbor, MI, where he spent nine years developing scalable processes for the preparation of drug candidates. In 2007, he moved to Groton, CT to continue his work as a process chemist and, during this period, he has
also worked in the area of biologics for 1.5 years on the preparation of linkers for bioconjugation processes. Javier currently holds a position in the Chemical Technology group at Pfizer, where he is involved in the applications of high-throughput screening to transition metal-catalyzed couplings. His research interests also include the development of catalytic processes that employ non-precious metals in coupling reactions.

Joshua R. Dunetz graduated from Haverford College in 2000 with a B.A. in Chemistry after undergraduate research with Professor Karin �kerfeldt. He received his Ph.D. in Organic Chemistry from MIT in 2005 under the guidance of Professor Rick Danheiser, and then completed postdoctoral studies with Professor William Roush at Scripps Florida. In early 2008, Joshua assumed his current position with Pfizer Chemical R&D in which he develops processes for the GMP manufacture of small molecules on gram to multikilogram scale.

Review:

“So, if you have any interest in transition metal-catalyzed cross-coupling reactions this book is for you.”  (Organic Process Research & Development Journal, 1 January 2014)

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Descripción Wiley-VCH Verlag GmbH. Hardback. Estado de conservación: new. BRAND NEW, Transition Metal-Catalyzed Couplings in Process Chemistry: Case Studies from the Pharmaceutical Industry, Javier Magano, Joshua R. Dunetz, Transition metal-catalyzed coupling reactions have a rich history that led to the awarding of the 2010 Nobel Prize in Chemistry to Professors Suzuki, Heck, and Negishi for their pioneering contributions to the field. The coming of age of this active area of research is showcased in this book through case studies in which process chemists from the pharmaceutical industry share their personal experiences developing their own transition metal-catalyzed couplings for the large-scale manufacture of active pharmaceutical ingredients. Authors from Pfizer, Merck, Boehringer-Ingelheim, Novartis, Amgen, GSK, AstraZeneca, and other companies describe the evolution of robust coupling processes from inception through early and late development, including commercial routes where applicable. This book covers a wide range of coupling transformations while capturing the lessons learned from each process. Every case study details the optimization of at least one transition metal-catalyzed coupling while elaborating on issues such as design of experiments, scalability and throughput, product purification, process safety, and waste management. The important issue of metal removal and the different technologies available to accomplish this goal are also addressed. Finally, a section covers novel technologies for cross-coupling with high potential for future applications on a large scale, such as microwave and flow chemistry as well as green cross-couplings performed in water. With Forewords by Stephen L. Buchwald, Massachusetts Institute of Technology, Trevor Laird, Editor of Organic Process Research and Development and Neal G. Anderson, Anderson's Process Solutions LLC. Nº de ref. de la librería B9783527332793

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Descripción Wiley VCH 2013-09-04, 2013. Estado de conservación: New. Brand new book, sourced directly from publisher. Dispatch time is 24-48 hours from our warehouse. Book will be sent in robust, secure packaging to ensure it reaches you securely. Nº de ref. de la librería NU-LBR-01217870

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Editor: Javier Magano (Chem. Research & Development, Pfizer Inc., Groton, CT, USA); Editor: Joshua R. Dunetz (Chemical Research & Development, Pfizer Inc., Groton, CT, USA)
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Descripción Estado de conservación: New. Publisher/Verlag: Wiley-VCH | Case Studies from the Pharmaceutical Industry | In this first one-stop reference on the topic focusing on case studies of large-scale applications authors from industry present the information that is otherwise hard to find in the current literature, showcasing project evolution from inception to early and late development. | Transition metal-catalyzed coupling reactions have a rich history that led to the awarding of the 2010 Nobel Prize in Chemistry to Professors Suzuki, Heck, and Negishi for their pioneering contributions to the field. The coming of age of this active area of research is showcased in thisbook through case studies in which process chemists from the pharmaceutical industry share their personal experiences developing their own transition metal-catalyzed couplings for the large-scale manufacture of active pharmaceutical ingredients.Authors from Pfizer, Merck, Boehringer-Ingelheim, Novartis, Amgen, GSK, AstraZeneca, and other companies describe the evolution of robust coupling processes from inception through early and late development, including commercial routes where applicable. This book covers a wide range of coupling transformations while capturing the lessons learned from each process. Every case study details the optimization of at least one transition metal-catalyzed coupling while elaborating on issues such as design of experiments, scalability and throughput, product purification, process safety, and waste management. The important issue of metal removal and the different technologies available to accomplish this goal are also addressed. Finally, a section covers novel technologies for cross-coupling with high potential for future applications on a large scale, such as microwave and flow chemistry as well as green cross-couplings performed in water.With Forewords by Stephen L. Buchwald, Massachusetts Institute of Technology, Trevor Laird, Editor of Organic Process Research and Development and Neal G. Anderson, Anderson's Process Solutions LLC. | FOREWORD 1FOREWORD 2FOREWORD 3INTRODUCTIONCOPPER-CATALYZED COUPLING FOR A GREEN PROCESSIntroductionSynthesis of Amino Acid 14Copper-Catalyzed CyclizationSustainabilitySummaryEXPERIENCES WITH NEGISHI COUPLINGS ON TECHNICAL SCALE IN EARLY DEVELOPMENTIntroductionSynthesis of LBT613 via Pd-Catalyzed Negishi CouplingElaboration of a Negishi Coupling in the Synthesis of PDE472Ni-Catalyzed Negishi Coupling with Catalytic Amounts of ZnCl2ConclusionsDEVELOPING PALLADIUM-CATALYZED ARYLATIONS OF CARBONYL-ACTIVATED C - H BONDSIntroductionSuzuki Approach to Side Chain InstallationArylation of Carbonyl-Activated C - H BondsPd Purging from APIConclusionsDEVELOPMENT OF A PRACTICAL SYNTHESIS OF NAPHTHYRIDONE P38 MAP KINASE INHIBITOR MK-0913IntroductionMedicinal Chemistry Approach to 1Results and DiscussionConclusionsPRACTICAL SYNTHESIS OF A CATHEPSIN S INHIBITORIntroductionSynthetic StrategySyntheses of Building BlocksSonogashira Coupling and Initial Purification of 1Salt SelectionConclusionsC - N COUPLING CHEMISTRY AS A MEANS TO ACHIEVE A COMPLICATED MOLECULAR ARCHITECTURE: THE AR-A2 CASE STORYA Novel Chemical EntityEvaluation of Synthetic Pathways: Finding the Best RouteEnabling C - N Coupling by Defining the Reaction SpaceFrom Synthesis to ProcessConcluding RemarksPROCESS DEVELOPMENT AND SCALE-UP OF PF-03941275, A NOVEL ANTIBIOTICIntroductionMedicinal Chemistry Synthesis of PF-03941275Synthesis of 5-Bromo-2,4-difluorobenzaldehyde (1)Synthesis of Amine 3Miyaura Borylation ReactionSuzuki - Miyaura CouplingBarbituric Acid CouplingChlorination and API IsolationConclusionsDEVELOPMENT OF A PRACTICAL NEGISHI COUPLING PROCESS FOR THE MANUFACTURING OF BILB 1941, AN HCV POLYMERASE INHIBITORIntroduction and BackgroundStille CouplingSuzuki CouplingNegishi CouplingComparison of Three Coupling ProcessesAPPLICATION OF A RHODIUM-CATALYZED, ASYMMETRIC 1,4-ADDITION TO THE KILOGRAM-SCALE MANUFACTURE OF A PHARMACEUTICAL INTERMEDIATEIntroductionEarly Developme. Nº de ref. de la librería K9783527332793

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Javier Magano
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Descripción Wiley VCH Verlag Gmbh Sep 2013, 2013. Buch. Estado de conservación: Neu. Neuware - Javier Magano received his Bachelor's Degree in organic chemistry from Complutense University in Madrid in 1987 and a Master s Degree in chemistry from the University of Michigan in 1990. After working for the oil industry in Spain for 3 years, he obtained a Master s Degree in rubber and polymer science from the School of Plastics and Rubber at the Center for Advanced Scientific Research in Madrid. In 1995 he moved back to the United States to carry out graduate work at the University of Michigan. In 1998 he joined Pfizer Inc. to work in the Chemical Research & Development group in Ann Arbor, MI, and currently in Groton, CT as senior scientist developing scalable processes for the production of drug candidates. 368 pp. Englisch. Nº de ref. de la librería 9783527332793

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