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Search for "imidazo[1,2-a]pyridine" in Full Text gives 26 result(s) in Beilstein Journal of Organic Chemistry.

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The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry

Marcus Baumann and
Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 1194–1219, doi:10.3762/bjoc.11.134

]. The synthesis of a small collection of imidazo[1,2-a]pyridine derivatives was realised through the application of different scavenger resins for in-line purification as well as a number of liquid handlers to orchestrate the library synthesis effort (Scheme 24). Using this semi-automated process a

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Graphical Abstract

Figure 1: Pharmaceutical structures targeted in early flow syntheses.

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Scheme 1: Flow synthesis of 6-hydroxybuspirone (9). Inserted photograph reprinted with permission from [45]. Copy...

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Figure 2: Configuration of a baffled reactor tube (left) and its schematic working principle (right).

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Scheme 2: McQuade’s flow synthesis of ibuprofen (16).

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Scheme 3: Jamison’s flow synthesis of ibuprofen sodium salt (17).

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Scheme 4: Flow synthesis of imatinib (23).

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Scheme 5: Flow synthesis of the potent 5HT1B antagonist 28.

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Scheme 6: Flow synthesis of a selective δ-opioid receptor agonist 33.

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Scheme 7: Flow synthesis of a casein kinase I inhibitor library (38).

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Scheme 8: Flow synthesis of fluoxetine (46).

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Scheme 9: Flow synthesis of artemisinin (55).

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Scheme 10: Telescoped flow synthesis of artemisinin (55) and derivatives (62–64).

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Scheme 11: Flow approach towards AZD6906 (65).

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Scheme 12: Pilot scale flow synthesis of key intermediate 73.

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Scheme 13: Semi-flow synthesis of vildagliptine (77).

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Scheme 14: Pilot scale asymmetric flow hydrogenation towards 83. Inserted photograph reprinted with permission...

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Figure 3: Schematic representation of the ‘tube-in-tube’ reactor.

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Scheme 15: Flow synthesis of fanetizole (87) via tube-in-tube system.

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Scheme 16: Flow synthesis of diphenhydramine^.HCl (92).

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Scheme 17: Flow synthesis of rufinamide (95).

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Scheme 18: Large scale flow synthesis of rufinamide precursor 102.

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Scheme 19: First stage in the flow synthesis of meclinertant (103).

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Scheme 20: Completion of the flow synthesis of meclinertant (103).

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Scheme 21: Flow synthesis of olanzapine (121) utilising inductive heating techniques.

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Scheme 22: Flow synthesis of amitriptyline·HCl (127).

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Scheme 23: Flow synthesis of E/Z-tamoxifen (132) using peristaltic pumping modules.

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Figure 4: Container sized portable mini factory (photograph credit: INVITE GmbH, Leverkusen Germany).

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Scheme 24: Flow synthesis of imidazo[1,2-a]pyridines 136 linked to frontal affinity chromatography (FAC).

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Figure 5: Structures of zolpidem (142) and alpidem (143).

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Scheme 25: Synthesis and screening loops in the discovery of new Abl kinase inhibitors.

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Figure 6: Schotten–Baumann approach towards LY573636^.Na (147).

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Scheme 26: Pilot scale flow synthesis of LY2886721 (146).

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Scheme 27: Continuous flow manufacture of alikiren hemifumarate 152.

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Review

Published 17 Jul 2015

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