Ammonium Chloride → 4-{3-Chloro-4-[2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-ethyl]-phenoxy}-benzonitrile

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Reaction Conditions

Reaction Steps

A 1.6 M solution of n-BuLi in hexane (1.05 ml) was added to 4-bromo-2-methylpyridin (CAS Reg. No. 22282-99-1, 289 mg) in THF (5 ml) at −78° C. The deep red solution was stirred for 10 min. A solution of 4-[3-chloro-4-(1-methyl-2-oxo-ethyl)-phenoxy]-benzonitrile (400 mg) in THF (5 ml) was added at −78° C. The mixture was allowed to warm to 0° C. and stirred for 15 min at that temperature. Saturated aqueous NH4Cl solution was added and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (200 mg) as a light yellow solid. MS (m/e)=379.2 [M+H+].

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