Sodium Iodide → (2-Methyl-4-{methyl-[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 (2-methyl-4-methylamino-phenoxy)-acetic acid ethyl ester (0.357 g, 1.6 mmol), 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (0.513 g, 1.76 mmol, WO02/28433) and NaI (0.24 g, 1.6 mmol) in DMF (4.8 ml) was added NaH (55% in oil, 0.105 g, 2.4 mmol). The reaction was stirred at RT for 2¾h, diluted with Et2O and extracted with aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to give 0.87 g (quantitative) of crude (2-methyl-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester as a yellow solid, MS: 479 (MH+).

Provenance & Evidence