β-Carbolines are a large group of natural and synthetic compounds characterized by a heterocyclic ring consisting of indole and pyridine. The biological effects of β-carbolines are diverse; for example, they showed antimalarial, antibacterial, and antiproliferative activity in vivo and in vitro. Assumed mechanism of antimalarial action of harmine, the best-studied β-carboline, is inhibition of the PfHsp90 protein. Primaquine is an 8-aminoquinoline antimalarial that has been used since 1952. This research describes synthesis of two new derivates of β-carboline and primaquine linked with 1,2,3-triazole bridge with the aim of obtaining derivatives with improved activity. The initial compound for the synthesis was tryptophan methyl ester, which was converted to tetrahydro-βcarboline 1 by the Pictet-Spengler reaction in a microwave reactor. Oxidation of compound 1 with Pd/C and Li2CO3 gave compound 2 (6-methoxyharman), which was converted to the corresponding alcohol 3 (6-hydroxyharman) by acid hydrolysis. The β-carboline alcohol 3 was converted to compound 4 with propargyl bromide. The target products (6 and 7) were synthesized from the propargylated β-carboline derivative 4 and primaquine azide 5 in the Huisgen 1,3-dipolar cycloaddition. The structures of synthesized compounds 6 and 7 were confirmed by standard analytical and spectroscopic methods (1H and 13C NMR, IR, MS), and their melting points were determined. Using the SwissADME software and Lipinski and Weber rules, compound 6 was found to satisfy almost all Lipinski and Weber rules and thus has the potential to be a new antimalarial drug. The biological activity of synthesized compounds 6 and 7 will be tested in further studies.