The alkylation of 4,4'-dihydroxybiphenyl (I) with ethyl bromoacetate (II) in the presence of sodium methoxide afforded the (biphenylyloxy)acetate (III). Heating of ester (III) with benzylamine (IV) at 85 C produced amide (V), which was subsequently reduced to amine (VI) by means of borane, generated in situ from NaBH4 and BF3. Finally, condensation of the secondary amine (VI) with methyl isocyanate gave rise to the title urea derivative.
The alkylation of 4,4'-dihydroxybiphenyl (I) with ethyl bromoacetate (II) in the presence of sodium methoxide afforded the (biphenylyloxy)acetate (III). Heating of ester (III) with m-fluorobenzylamine (IV) at 85 C produced amide (V), which was subsequently reduced to amine (VI) by means of borane, generated in situ from NaBH4 and BF3. Finally, condensation of the secondary amine (VI) with methyl isocyanate gave rise to the title urea derivative.