Dimethylformamide → 7-(2-{[Di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide

Participants

Reaction Steps

A mixture of 7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid (2.0 g), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (1.19 g), 1-hydroxybenzotriazole ammonium salt (943 mg) and N,N-dimethylformamide (20 mL) was stirred at room temperature for 9 hr. The reaction solution was allowed to cool to room temperature, and concentrated under reduced pressure. Water was added to the residue, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with aqueous citric acid solution, water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=30:70-70:30, volume ratio) to give the title compound (1.37 g, yield 69%) as an orange oil. MS 643 (MH+).

Provenance & Evidence