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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 the 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 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.