3-(2-Chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-(5-methyl-pyrazin-2-yl)-butan-2-ol → 3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenol

Participants

Reaction Steps

A solution of 3-(2-chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-(5-methyl-pyrazin-2-yl)-butan-2-ol (Example 1, 60 mg, 0.17 mmol) in aqueous HBr (48%, 2 mL) was refluxed for 3 h. The reaction mixture was poured into ice/water, and extracted (ethyl acetate). The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was taken up in methanol and purified (reversed-phase, preparative HPLC, Agilent Zorbax XdB-C18 column, solvent gradient 5-95% CH3CN in 0.1% TFA[aq]) to give the title compound (44 mg). MS (m/e)=347.1 (MH+).

Provenance & Evidence