Dimethylformamide → Ethyl 7-[(6-chloropyridin-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate

Participants

Reaction Steps

A mixture of ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (1.39 g), 2-(bromomethyl)-6-chloropyridine (840 mg), potassium carbonate (1.02 g) and N,N-dimethylformamide (20 mL) was stirred at room temperature for 2.5 hr. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained crude product was subjected to basic silica gel column chromatography (ethyl acetate:hexane=10:90-65:35, volume ratio), and the obtained solid was washed with diethyl ether to give the title compound (1.0 g, yield 54%) as white crystals. MS 501 (MH+).

Provenance & Evidence