Water → HCID 59296184, compound

Participants

Reaction Steps

To a solution of 2.255 g of [4-butyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-yl]-methanol in 25 ml of dimethylformamide was added 0.286 g of a 60% dispersion of sodium hydride in mineral oil. After stirring for 15 minutes, 3 g of 4-bromomethyl-2-fluoro-benzonitrile was added. The resulting mixture was stirred at room temperature overnight, then poured into water, extracted with diisopropyl ether. The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (heptane 95/ethyl acetate 5) to give 0.6 g of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxymethyl]-2-fluoro-benzonitrile, which was transformed into 3-{4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxymethyl]-2-fluoro-phenyl}-4H-[1,2,4]oxadiazol-5-one according to the method described in example 1.

Provenance & Evidence