Multistep synthesis

Multistep Continuous-Flow Processes for the Preparation of Heterocyclic Active Pharmaceutical Ingredients

Romaric Gérardy, Jean-Christophe M. Monbaliu

• Center for Integrated Technology and Organic Synthesis, Department of Chemistry, University of Liège, Liège, Belgium

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Telescoped continuous flow generation of a library of highly substituted 3-thio-1,2,4-triazoles.

Mariana C. F. C. B. Damião^a, Renan Galaverna^a, Alan P. Kozikowski^b, James Eubanks^c, Julio C. Pastre^a

• ^a Institute of Chemistry, University of Campinas - UNICAMP, PO Box 6154 - Zip Code 13083-970, Campinas, SP, Brazil
• ^b StarWise Therapeutics LLC - University Research Park – Zip Code 53719-1235, Madison, Wisconsin, USA
• ^c Division of Genetics and Development - Krembil Research Institute – Zip Code M5T 2S8, Toronto, Ontario, Canada

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A Short Multi-step Flow Synthesis of a Potential Spirocyclic Fragrance Component

Ian R. Baxendale*

• Department of Chemistry, University of Durham, South Road, Durham, DH1 3LE, UK

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A Concise Flow Synthesis of Efavirenz†

Dr. Camille A. Correia¹, Dr. Kerry Gilmore¹, Prof. Dr. D. Tyler McQuade³, Prof. Dr. Peter H. Seeberger^{1 2 *}

• ¹ Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam (Germany)
• ² Institute for Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin (Germany)
• ³ Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306 (USA)

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Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent

Catherine J. Smith, Christopher D. Smith, Nikzad Nikbin, Steven V. Ley, Ian R. Baxendale

• Innovative Technology Centre, Cambridge, UK

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Integration of enabling methods for the automated flow preparation of piperazine-2-carboxamide

Richard J. Ingham¹, Claudio Battilocchio¹, Joel M. Hawkins², Steven V. Ley¹

• ¹ Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK
• ² Pfizer Worldwide Research and Development, Eastern Point Road, Groton, CT 06340, USA

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Applying Flow Chemistry: Methods, Materials, and Multistep Synthesis

D. Tyler McQuade^{1 3}, Peter H. Seeberger^{1 2}

• ¹ Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces
• ² Institute for Chemistry and Biochemistry, Freie Universität Berlin,
• ³ Department of Chemistry and Biochemistry, Florida State University

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An expeditious synthesis of imatinib and analogues utilising flow chemistry methods

Mark D Hopkin, Ian Baxendale, Steven.V.Ley

• Dept of Chemistry, University of Cambridge, UK

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A Multi-Step Continuous Flow Process for the N-Demethylation of Alkaloids

Yuji Nakano¹, G. Paul Savage¹, Simon Saubern¹, Peter J. Scammells², Anastasios Polyzos¹

• ¹ CSIRO Materials Science and Engineering, Victoria, Australia.
• ² Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, Victoria, Australia.

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A Two-Stage Continuous-Flow Synthesis of Spirooxazine Photochromic Dyes

Mark York¹²³, Adriana Edenharter¹

• ¹CSIRO Materials Science and Engineering, Clayton, Vic. 3169, Australia.
• ²Cooperative Research Centre for Polymers, Notting Hill, Vic. 3168, Australia.
• ³Advanced Polymerik Pty Ltd, Notting Hill, Vic. 3168, Australia.

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Synthesis of an H3 Antagonist via Sequential One-Pot Additions of a Magnesium Ate Complex and an Amine to a 1,4-Ketoester followed by Carbonyl-Directed Fluoride Addition

Joel M. Hawkins, Pascal Dubé, Mark T. Maloney, Lulin Wei. Marcus Ewing, Stephen M. Chesnut, Joshua R. Denette, Brett M. Lillie, Rajappa Vaidyanathan

• Pharmaceutical Sciences, Pfizer Inc., Groton, USA

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Scale-Up of Flow-Assisted Synthesis of C2-Symmetric Chiral PyBox Ligands

Claudio Battilocchio^1,3, Marcus Baumann¹, Ian R. Baxendale¹, Mariangela Biava³, Matthew O. Kitching¹, Steven V. Ley¹, Rainer E. Martin^*2, Stephan A. Ohnmacht², Nicholas D. C. Tappin¹

• ¹Department of Chemistry, University of Cambridge, UK
• ²F. Hoffmann-La Roche Ltd., Pharmaceuticals Division, Basel, Switzerland
• ³Department of Pharmaceutical Chemistry and Technology, Sapienza University of Rome, Italy

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Synthesis of a Drug-Like Focused Library of Trisubstituted Pyrrolidines Using Integrated Flow Chemistry and Batch Methods

Marcus Baumann¹, Ian R. Baxendale¹, Steven V. Ley¹, Christoph Kuratli², Rainer E. Martin², Josef Schneider²

• ¹Innovative Technology Centre, University of Cambridge, U.K.
• ²F. Hoffmann-La Roche Ltd., Basel, Switzerland

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Synthesis of (+)-Dumetorine and Congeners by Using Flow Chemistry Technologies

Elena Riva², Anna Rencurosi¹, Stefania Gagliardi¹, Daniele Passarella², Marisa Martinelli^1*

• ¹NiKem Research S.r.l., Milan, Italy
• ²Università degli Studi di Milano,Milan, Italy

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Preparation of fluoxetine by multiple flow processing steps

Batoul Ahmed-Omer, Adam J. Sanderson

• Eli Lilly and Co. Ltd.
• Lilly Research Centre, UK.

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Diastereoselective Chain-Elongation Reactions Using Microreactors for Applications in Complex Molecule Assembly

Catherine F. Carter¹, Heiko Lange¹, Daiki Sakai², Ian R. Baxendale¹, Steven V. Ley¹

• ¹Innovative Technology Centre, University of Cambridge, UK, CB2 1EW, UK
• ²Mitsubishi Tanabe Pharma Corporation, Yokohama, Japan

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A fully automated, multistep flow synthesis of 5-amino-4-cyano-1,2,3-triazoles

Catherine J. Smith, Nikzad Nikbin, Steven V. Ley, Heiko Lange, Ian R. Baxendale

• Innovative Technology Centre, Cambridge, UK

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A breakthrough method for the accurate addition of reagents in multi-step segmented flow processing

Heiko Lange¹, Catherine F. Carter¹, Mark D. Hopkin¹, Adrian Burke², Jon G. Goode², Ian R. Baxendale¹, Steven V. Ley¹

• ¹Innovative Technology Centre, University of Cambridge, UK
• ²Mettler-Toledo AutoChem UK

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Safe and Reliable Synthesis of Diazoketones and Quinoxalines in a Continuous Flow Reactor

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Preparation of arylsulfonyl chlorides by chlorosulfonylation of in situ generated diazonium salts using a continuous flow reactor

Laia Malet-Sanz, Julia Madrzak, Steven V.Ley, Ian R.Baxendale

• Innovative Technology Centre, University of Cambridge

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Synthesis of Highly Substituted Nitropyrrolidines, Nitropyrrolizines and Nitropyrroles via Multicomponent-Multistep Sequences within a Flow Reactor

Marcus Baumann, Ian R. Baxendale, Andreas Kirschning, Steven V. Ley^*, Jens Wegner

• Department of Chemistry, University of Cambridge

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Flow synthesis of tricyclic spiropiperidines as building blocks for the histrionicotoxin family of alkaloids

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The application of flow microreactors to the preparation of a family of casein kinase I inhibitors

Francesco Venturoni, Nikzad Nikbin, Steven V. Ley, Ian R. Baxendale

• Innovative Technology Centre, Department of Chemistry, University of Cambridge

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A highly efficient flow reactor process for the synthesis of N-Boc-3,4-dehydro-l-proline methyl ester

Lucia Tamborini, Paola Conti, Andrea Pinto, Carlo De Micheli

• Dipartimento di Scienze Farmaceutiche ‘Pietro Pratesi’,
• Università degli Studi di Milano, Italy

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Multi-Step Synthesis by Using Modular Flow Reactors: The Preparation of YneOnes and Their Use in Heterocycle Synthesis

Ian R. Baxendale¹, Søren C. Schou², Jörg Sedelmeier¹, Steven V. Ley¹

• ¹ITC, Department of Chemistry, University of Cambridge
• ²LEO Pharma, Medicinal Chemistry Research, Denmark

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Multistep Synthesis Using Modular Flow Reactors: Bestmann-Ohira Reagent for the Formation of Alkynes and Triazoles

Ian R. Baxendale¹, Steven V. Ley¹, Andrew C. Mansfield², Christopher D. Smith¹

• ¹ITC, Department of Chemistry, University of Cambridge,
• ²Pfizer Global R&D Research Centre, Sandwich, (UK)

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Efficient Continuous Flow Synthesis of Hydroxamic Acids and Suberoylanilide Hydroxamic Acid Preparation

E. Riva¹, S. Gagliardi², Caterina Mazzoni², M. Martinelli², D. Passarella¹, D. Vigo², A. Rencurosi²

• ¹Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Italy
• ²NiKem Research S.r.l., Milan, Italy

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Tagged phosphine reagents to assist reaction work-up by phase-switched scavenging using a modular flow reactor

Christopher D. Smith, Ian Baxendale, Geoffrey Tranmer, Marcus Baumann, Stephen Smith, Russell Lewthwaite, Steven V. Ley

• Department of Chemistry, University of Cambridge, UK

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A flow process for the multi-step synthesis of the alkaloid natural product oxomaritidine: a new paradigm for molecular assembly

Ian R. Baxendale, Jon Deeley, Charlotte M. Griffiths-Jones, Steven V. Ley, Steen Saaby, Geoffrey K. Tranmer

• Innovative Technology Centre, University of Cambridge

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