Sodium Iodide → (2-(3-Methoxy-propyl)-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester

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Reaction Steps

To 0.216 g (0.77 mmol) of the above prepared [2-(3-methoxy-propyl)-4-methylamino-phenoxy]-acetic acid ethyl ester, dissolved in 2.4 ml of abs. DMF, were added successively at 0° C. 0.037 g of NaH (60% in mineral oil, 1.2 eq.), 0.115 g (1 eq.) of NaI and 0.215 g (0.96 eq.) of 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (WO02/28433). The reaction was allowed to proceed for 5 min at 0° C. and for 0.5 h at ambient temperature. Pouring onto crashed ice/aqueous 10% KHSO4, twofold extraction with EtOAc, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/EtOAc=78/22), yielded 0.284 g of the title compound as light yellow oil, MS: 537.5 (MH)+.

Provenance & Evidence