N,N,N',N'-Tetramethylazodicarboxamide → [rac]-(4-{2-Methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-indol-1-yl)-acetic acid tert-butyl ester

Participants

Reaction Steps

To an ice cold solution of (4-hydroxy-indol-1-yl)-acetic acid tert-butyl ester (49 mg, 0.2 mmol), [rac]-2-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-ol [62 mg, 0.2 mmol; PCT Int. Appl. (2002), WO 02/062774 A1] and tributylphosphine (70 μl, 0.3 mmol) in tetrahydrofuran (3 ml) was added N,N,N′,N′-tetramethyl azodicarboxamide (51 mg, 0.3 mmol) under an argon atmosphere. The cooling bath was removed and stirring continued for 14 h. Filtration over celite and evaporation of the solvent under reduced pressure gave a yellow oil which was purified by column chromatography (silica gel, heptane/AcOEt) to give 13 mg (24 μmol, 12%) of the title compound as yellow oil.

Provenance & Evidence