2-Chloromethyl-5-(4-iodophenyl)-[1,3,4]oxadiazole (Intermediate 7) (48 mg, 0.15 mmol), serinol (206 mg, 2.25 mmol) and potassium iodide (25 mg, 0.15 mmol) were dissolved in dimethylformamide (1 ml) and stirred for 18 hours at 20° C. The reaction was evaporated to dryness in vacuo and the product was flushed through a 10 g silica SPE cartridge, eluting with 95:5 ethyl acetate:methanol, to remove inorganic material. Without further purification the crude product was dissolved in 1,2 dimethoxyethane (4 ml). 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) were added. The reaction was heated under nitrogen at 80° C. for 18 hours. Solvent was removed in vacuo and the residue was purified by mass-directed HPLC to yield the desired product.
