Sodium Iodide → HCID 66699473, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenol (93 mg, obtained in Example 93, step 6) in DMF (2 mL) was added to a suspension of NaH (60% in mineral oil, 24 mg) in DMF (1 mL) over 10 minutes. Stirring was continued for 30 minutes at r.t. The mixture was cooled to 0° C. and (4-chloromethyl-pyrazol-1-yl)-acetic acid methyl ester (61 mg, obtained in Example 103, step 4) dissolved in DMF (2 mL) was added dropwise over a period of 5 minutes. Stirring was continued for 2 hours at r.t. followed by the addition of NaI (3 mg). The mixture was heated to 50° C. overnight. The reaction mixture was cooled, poured into ice and extracted two times with chloroform. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a light yellow gum (13 mg, 10%). MS (m/e)=498.2 [MH−].

Provenance & Evidence