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

Participants

Reaction Steps

To an ice-cooled and stirred solution of crude (4-ethylamino-phenoxy)-acetic acid ethyl ester (0.243 g, containing 0.214 g, 0.96 mmol), 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (0.308 g, 1.05 mmol, WO02/28433) and NaI (0.144 g, 0.96 mmol) in DMF (3 ml) was added NaH (55% in oil, 0.063 g, 1.44 mmol). The reaction was stirred at RT for 4 h, water was added and diluted with Et2O and extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3, dried (Na2SO4) and evaporated to give 0.32 g (70%) of crude (4-{ethyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester as an orange oil, MS: 479 (MH+).

Provenance & Evidence