6-Fluoroindole (CAS number 399-51-9) is a fluorinated (6-position) indole, a benzene ring fused pyrrole heterocycle. 6-Fluoroindole is an antimicrobial which works by interfering with the quorum sensing system of the pathogens. 6-Fluoroindole inhibits the biofilm formation that causes infections.
6-Fluoroindole can be easily functionalized with Bpin groups (pinacol boronate) at 2-, 3-, 4-, 5- and 7-positions selectively with iridium-catalyzed borylation and bismuth-catalyzed protodeboronation. The modification to 6-fluoroindole allows late-stage functionalization on different positions of the molecule, expanding the molecular library for drug discovery.
6-Fluoroindole is also used to label bacteria cells (Escherichia coli) in order to study the protein-protein interaction in vitro with 19F NMR and 15N-1H HSQC (heteronuclear single quantum coherence) NMR.