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Synthesis 2021; 53(06): 1174-1180
DOI: 10.1055/s-0040-1706299
paper

Convergent Synthesis of Immune Inhibitor IMMH002

Si Chen 
,
Zeyu Shi
,
Qiong Xiao∗
,
Dali Yin
This work was financially supported by the National Key R & D Program­ of China (No. 2018YFC1706403), Drug Innovation Major Project (No. 2018ZX09711001-005.China), CAMS Collaborative Innovation Project (No. 2019-I2M-1-005, China), and Disciplines Construction Project (No. 201920200802, China).
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Abstract

A convergent synthesis of IMMH002 in 36% overall yield starting from bromobenzene is described with a key Suzuki–Miyaura cross-coupling reaction used to provide a crucial intermediate. The route does not require column chromatography and solves the most intractable quality problem caused by a homologue by-product in the original linear synthesis. Furthermore, reducing the use of Lewis acid mediated reactions improves the environmental impact of the synthesis and reduces overall waste. The new route described herein is more efficient, convenient, reliable, and economically more viable when compared to the previously reported linear route.

Key words

IMMH002 - S1P1 - convergent synthesis - Suzuki–Miyaura coupling reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706299.
  • Supporting Information


Publication History

Received: 29 July 2020

Accepted after revision: 25 August 2020

Article published online:
14 October 2020

© 2020. Thieme. All rights reserved

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