Thioanisole → HCID 67119187, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled and stirred solution of triphenylphosphine oxide (0.43 g) in acetonitrile (8 mL) was added trifluoromethanesulfonic anhydride (0.13 mL), and the mixture was stirred at 4° C. for 30 min, followed by an addition of a solution of N-[2-(benzylsulfanyl)-3,3-dimethoxypropyl]-7-(2-methoxy-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide (0.25 g) and thioanisole (0.093 mL) in acetonitrile (5 mL). After stirring at 4° C. for 30 min, the reaction mixture was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution, and the organic layer was washed with brine, dried (MgSO4), filtered, and concentrated. The resulting precipitate was removed by filtration and washed with ethyl acetate-hexane. The combined filtrate and washings were concentrated and the residue was purified by basic silica gel chromatography (ethyl acetate:hexane=25:75 to 35:65, volume ratio) and then by silica gel chromatography (ethyl acetate:hexane=25:75 to 80:20) to give a colorless oil, which was crystallized from diethyl ether-hexane to give the title compound (21 mg, 10%) as colorless crystals. MS 535 (MH+). mp 109-112° C.

Provenance & Evidence