We Additionally, an efficient reaction route toward the cyclization precursors from commercially available and non-expensive 2-iodoaniline was developed. The order of reaction steps and conditions of each step were optimized to gain optimal results with respect to the yield and purity of the compounds and structures of at least one product of each reaction step were confirmed via X-ray crystallography. The combination of the developed reaction route towards F-tagged precursors with the newly found cyclization reaction resulted in a fast and expedient process to synthesize novel indole derivatives with diverse modifications in positions N1 and C2. Using this process, a small library of 16 novel, F-tagged 3-acylindole derivatives, as well as three additional derivatives bearing other fluorine-containing acyl moieties, was synthesized. F{1H}-13 C{1H}-HSQC NMR measurements were used to characterize all 16 F-tagged compounds, providing a fast and reliable method to gain the required information on the centre of all 13 C nuclei in the isolated compounds. The fluorine tag should be easily cleavable from the products, yielding 3-carboxylic acid or 3-ester derivatives of the synthesized substituted indoles. This would make them valuable candidates for different biological screenings, since the indole core is an important building block present in many biologically active compounds.