Potassium Iodide → 6-Methyl-4'-(5-methylaminomethyl-[1,3,4]oxadiazol-2-yl)biphenyl-3-carboxylic acid cyclopropylamide

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2-Chloromethyl-5-(4-iodophenyl)-[1,3,4]oxadiazole (Intermediate 7) (48 mg, 0.15 mmol) and potassium iodide (25 mg, 0.15 mmol) were dissolved in 2M methylamine in tetrahydrofuran (2 ml) and stirred for 18 hours at 20° C. The reaction was evaporated to dryness in vacuo and the product was purified on a 10 g silica SPE cartridge (stepped solvent gradient 80:20 ethyl acetate:cyclohexane, 100% ethyl acetate, 95:5 ethyl acetate:methanol). The resulting material was dissolved in 1,2 dimethoxyethane (4 ml) with tetrakis(triphenylphosphine)palladium(0) (16 mg, 0.014 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 17) (0.15 mmol) and 1M aqueous sodium carbonate (0.15 ml, 0.15 mmol). The reaction was heated under nitrogen at 80° C. for 18 hours. The solvent was removed in vacuo and the residue was purified by silica biotage chromatography eluting with 95:5 ethyl acetate:methanol.

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