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

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Reaction Conditions

Reaction Steps

To an ice-cooled and stirred solution of (4-tert-butoxycarbonylamino-2-methyl-phenoxy)-acetic acid methyl ester (1.00 g, 3.39 mmol, example 17.3), sodium iodide (0.51 g, 3.39 mmol) and 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (1.09 g, 3.72 mmol, WO02/28433) in DMF (10 ml) was added within 10 min NaH (0.19 g, 55% in oil, 4.40 mmol). The reaction was stirred at 0° C. for 2 h, 30 min at RT and then neutralized with chilled aqueous 10% KHSO4 and extracted with aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to give 2.14 g of (4-{tert-butoxycarbonyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-2-methyl-phenoxy)-acetic acid methyl ester, MS: 551.3 (MH+).

Provenance & Evidence