238. Development of a Continuous Flow Synthesis of FGIN-1-27 Enabled by in-line 19F NMR Analyses and Optimization Algorithms

N. Vasudevan, Ehu Camille Aka, Elvina Barré, Eric Wimmer, Daniel Cortés-Borda, Patrick Giraudeau, Jonathan Farjon, Mireia Rodriguez-Zubiri and François-Xavier Felpin; Reaction Chemistry & Engineering; (2021); DOI: 10.1039/D1RE00220A

A straightforward continuous flow synthesis of FGIN-1-27, a compound with potent anxiolytic effects, is described from inexpensive and commercially available starting materials. The four-step synthesis includes a direct C-H arylation of an indole with an arenediazonium salt. The continuous flow route was developed thanks to the use of enabling technologies such as a real-time in-line benchtop 19F NMR analysis and an optimization algorithm assisting the decision-making process. These enabling technologies increase the process safety and minimize the number of experiments required in optimization campaigns.