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An efficient method has been developed for the synthesis of 2-amino-4-(4-fluoro-3-(2- fluoropyridin-3-yl)phenyl)-4-(4-methoxy-3-methylphenyl)-1-methyl-1H-imidazol-5(4H)-one, a potent BACE1 inhibitor for the potential treatment of Alzheimer's Disease. The new method features a Friedel-Crafts reaction between 3-bromo-4-fluorophenylacetic acid and 2- methoxytoluene followed by DMSO mediated α-oxidation of the resulting 1,2-diarylethanone to give an α-diketone. Subsequent aminohydantoin formation and Suzuki coupling led to the target molecule in greater than 70% overall yield.

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An efficient synthesis of 2-amino-4-(4-fluoro-3-(2-fluoropyridin-3-yl)phenyl)-4-(4-methoxy-3-methylphenyl)-1-methyl-1H-imidazol-5(4H)-one, a potent BACE1 inhibitor