A New Flow Methodology for the Expedient Synthesis of Drug-Like 3-Aminoindolizines

Authors: Lange, Paul P.; Bogdan, Andrew R.; James, Keith

Source: Advanced Synthesis & Catalysis, Volume 354, Number 13, 17 September 2012 , pp. 2373-2379(7)

Publisher: Wiley-Blackwell

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Abstract:

<title type="main">Abstract</title>

A flow-based synthesis of diversely functionalized indolizines and their aza-analogues is described. These drug-like heterocycles were generated via a tandem Sonogashira/cycloisomerization sequence, starting from widely available 2-bromopyridines and alkynes, employing a simple catalyst system together with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as base. The use of flow technology allows a straightforward and rapid access to a variety of novel compounds, and enables linear scale-up from milligram- to gram-scales without a decrease in yield.

Document Type: Communications

DOI: http://dx.doi.org/10.1002/adsc.201200316

Affiliations: 1: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA, phone: (+1)-858-784-2507, Fax: (+1)-858-784-7550

Publication date: 2012-09-17