Ethyl Acetate → HCID 46939950, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzoic acid (Example 26, 150 mg, 0.238 mmol) in ethyl acetate (5 mL) at 0° C. was added CDI (68 mg, 0.42 mmol). The mixture was stirred for 30 min. at 0° C. Additional ethyl-2-oxoiminooxamate (55 mg, 0.42 mmol) was added. The reaction mixture was washed with water, sat aq NaHCO3 and brine, dried over MgSO4, filtered and concentrated. The residue yellow waxy solid was dissolved in N,N-dimethylformamid (2 mL) and stirred for 3 h at 90° C. and 2 h at 140° C. The mixture was cooled to room temperature, poured in water (20 mL) and extracted twice with AcOEt. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, heptane/AcOEt 3:1) to give title compound (113 mg) as a white waxy solid. MS (m/e)=490.0 [M+H+].

Provenance & Evidence