Tributylphosphine → HCID 58236999, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-(2-methoxy-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide (874 mg) in tetrahydrofuran (20 mL) was added Lawesson's reagent (845 mg) at room temperature. The mixture was stirred at 50° C. for 45 min, and then cooled to room temperature. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=50:50 to 100:0, volume ratio) to give a yellow amorphous solid. To a solution of the solid in tetrahydrofuran (20 mL) were added ethyl 2-butynoate (0.507 mL) and tributylphosphine (0.652 mL). The whole was stirred at 50° C. for 45 min. The mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=50:50 to 100:0) to give the title compound (531 mg, 46%) as a brown amorphous solid. MS 547 (MH+).

Provenance & Evidence