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Continuous Flow Total Synthesis of Rufinamide

By Zhang, Ping; Russell, M. Grace; Jamison, Timothy F.

Published on

Abstract

Small molecules bearing 1,2,3-triazole functionalities are important intermediates and pharmaceuticals. Common methods to access the triazole moiety generally require the generation and isolation of organic azide intermediates. Continuous flow synthesis provides the opportunity to synthesize and consume the energetic organoazides, without accumulation thereof. In this report, we described a continuous synthesis of the antiseizure medication rufinamide. This route is convergent and features copper tubing reactor-catalyzed cycloaddition reaction. Each of the three chemical steps enjoys significant benefits and has several advantages by being conducted in flow. The total average residence time of the synthesis is approximately 11 min, and rufinamide is obtained in 92% overall yield.

Journal

Organic Process Research & Development. Volume 18, 2014, 1567–1570

DOI

10.1021/op500166n

Type of publication

Peer-reviewed journal

Affiliations

  • Massachusetts Institute of Technology
  • Franciscan University of Steubenville

Article Classification

Research Article

Classification Areas

  • API

Tags