All the newly designed compounds were synthesized as outlined in Scheme 1. Compounds 5a-5o were prepared in two-step chemical synthesis according to the previously described methods . The initial step involved the Friedländer condensation of 2-amino-5-bromobenzonitrile 1 in the presence of cyclohexanone 2 and Lewis acid (ZnCl2), affording 7-bromotacrine formation (3). The reaction proceeded under microwave-assisted conditions. Finally, the palladium-catalyzed cross-coupling reactions between the appropriately substituted arylboronic acids 4a-4o and 3 were carried out in the mixture of THF/H2O, resulting in compounds 5a-5o in good overall yields (11-64%). Compound 7 was prepared in one-step chemical synthesis, where intermediate 3 reacted with deuterium gas in deuterated methanol and triethylamine. The reaction mixture was catalyzed by 10% Pd/C. All the final compounds were characterized by 1 H and 13 C NMR, HRMS, and LC-UV analysis confirmed their purity to be higher than 95%. Deuterium enrichment (> 0.97 atom D per molecule) was determined from the mass spectrum (all spectra are available at Supporting Information).