Sodium hydride → {4-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester

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Reaction Steps

To a solution of 4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-1H-indole (50 mg, 130 μmol) and bromo-acetic acid tert-butyl ester (20 μl, 140 μmol) in DMF (4 ml) was added sodium hydride (55%, 8 mg, 176 μmol) under an argon atmosphere at 0° C. The mixture was naturally warmed to room temperature, stirred for 72 h, poured onto 1 N HCl/ice water 1/1 and extracted three times with dichloromethane. The combined organic layers were washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, heptane/AcOEt) to give 50 mg (99 μmol, 77%) of the title compound as light yellow oil.

Provenance & Evidence