An expeditious synthesis of imatinib and analogues utilising flow chemistry methods

被引：78

作者：

Hopkin, Mark D. ^{[1
]}

Baxendale, Ian R. ^{[2
]}

Ley, Steven V. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

[2] Univ Durham, Dept Chem, Durham DH1 3LE, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 11期

基金：

英国工程与自然科学研究理事会;

关键词：

RHODIUM-CATALYZED HYDROFORMYLATION; CROSS-COUPLING REACTIONS; ENABLING TECHNOLOGY; AMINATION; EFFICIENT; REACTORS; LIGANDS; AMINES;

D O I：

10.1039/c2ob27002a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A flow-based route to imatinib, the API of Gleevec, was developed and the general procedure then used to generate a number of analogues which were screened for biological activity against Abl1. The flow synthesis required minimal manual intervention and was achieved despite the poor solubility of many of the reaction components.

引用

页码：1822 / 1839

页数：18

共 46 条

[1] An Integrated Flow and Batch-Based Approach for the Synthesis of O-Methyl Siphonazole
Baumann, Marcus
Baxendale, Ian R.
Brasholz, Malte
Hayward, John J.
Ley, Steven V.
Nikbin, Nikzad
[J]. SYNLETT, 2011, (10) : 1375 - 1380
[2] The flow synthesis of heterocycles for natural product and medicinal chemistry applications
Baumann, Marcus
Baxendale, Ian R.
Ley, Steven V.
[J]. MOLECULAR DIVERSITY, 2011, 15 (03) : 613 - 630
[3] Multi-Step Synthesis by Using Modular Flow Reactors: The Preparation of Yne-Ones and Their Use in Heterocycle Synthesis
Baxendale, Ian R.
Schou, Soren C.
Sedelmeier, Joerg
Ley, Steven V.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) : 89 - 94
[4] Preparation of the neolignan natural product grossamide by a continuous-flow process
Baxendale, IR
Griffiths-Jones, CM
Ley, SV
Tranmer, GK
[J]. SYNLETT, 2006, (03) : 427 - 430
[5] A new class of easily activated palladium precatalysts for facile C-N cross-coupling reactions and the low temperature oxidative addition of aryl chlorides
Biscoe, Mark R.
Fors, Brett P.
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (21) : 6686 - +
[6] The Continuous-Flow Synthesis of Styrenes Using Ethylene in a Palladium-Catalysed Heck Cross-Coupling Reaction
Bourne, Samuel L.
Koos, Peter
O'Brien, Matthew
Martin, Benjamin
Schenkel, Berthold
Baxendale, Ian R.
Ley, Steven V.
[J]. SYNLETT, 2011, (18) : 2643 - 2647
[7] A New Enabling Technology for Convenient Laboratory Scale Continuous Flow Processing at Low Temperatures
Browne, Duncan L.
Baumann, Marcus
Harji, Bashir H.
Baxendale, Ian R.
Ley, Steven V.
[J]. ORGANIC LETTERS, 2011, 13 (13) : 3312 - 3315
[8] Continuous Flow Processing of Slurries: Evaluation of an Agitated Cell Reactor
Browne, Duncan L.
Deadman, Benjamin J.
Ashe, Robert
Baxendale, Ian R.
Ley, Steven V.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (03) : 693 - 697
[9] Buerger H. M., 2002, World Pat, Patent No. [2002 022 597, 2002022597]
[10] Diastereoselective Chain-Elongation Reactions Using Microreactors for Applications in Complex Molecule Assembly
Carter, Catherine F.
Lange, Heiko
Sakai, Daiki
Baxendale, Ian R.
Ley, Steven V.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (12) : 3398 - 3405

← 1 2 3 4 5 →