Development of a Large-Scale Cyanation Process Using Continuous Flow Chemistry en Route to the Synthesis of Remdesivir

• Tiago Vieira^1*
• Andrew C. Stevens^1*
• Andrei Chtchemelinine²
• Detian Gao¹
• Pavel Badalov¹
• Lars Heumann²

• ¹Gilead Alberta ULC, 1021 Hayter Road, Edmonton, Alberta T6S 1A1, Canada
• ²Gilead Sciences, Inc. 333 Lakeside Drive, Foster City, California 94404, United States

The implementation of cyanation chemistry at manufacturing scales using batch equipment can be challenging due to the hazardous nature of the reagents employed, and the tight control of reaction parameters, including cryogenic temperatures, that help to afford acceptable selectivity and conversion for the desired reaction. Application of continuous flow chemistry offers a means to mitigate the risk associated with handling large amounts of hazardous reagents and to better control the reaction parameters. A case study describing the cyanation of a glycoside using continuous flow chemistry towards the synthesis of the drug candidate remdesivir is presented.

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