Sodium Iodide → (2-Methyl-4-{methyl-[5-(4-trifluoromethyl-phenyl)-pyrazin-2-ylmethyl]-amino}-phenoxy)-acetic acid methyl ester

Participants

Reaction Steps

A suspension of 53 mg (0.39 mmol) potasium carbonate and 52 mg (0.35 mmol) sodium iodide and 73 mg (0.35 mmol) (2-methyl-4-methylamino-phenoxy)-acetic acid methyl-ester (example 5F) in 2 ml of DMSO was treated with 32 mg (0.12 mmol) of 2-chloromethyl-5-(4-trifluoromethyl-phenyl)-pyrazine (example 33E]). After 1.5 h at RT, the second portion of 32 mg (0.12 mmol) of 2-chloromethyl-5-(4-trifluoromethyl-phenyl)-pyrazine was added. The third part was added after 2 h. The reaction mixture was stirred for total 19 h at RT. It was then taken up in ether and washed with aqueous 10% KHSO4-solution and water. The organic phase was washed with NaCl (10%), dried (Na2SO4) and evaporated. Purification by flash chromatography (SiO2, heptane/AcOEt=9/1) gave 126 mg of pure (2-methyl-4-{methyl-[5-(4-trifluoromethyl-phenyl)-pyrazin-2-ylmethyl]-amino}-phenoxy)-acetic acid methyl ester.

Provenance & Evidence