Tributylphosphine → HCID 70963867, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-7-(1-methylethoxy)-1H-indole-2-carboxamide (1.0 g), Lawesson's reagent (1.25 g) and tetrahydrofuran (100 mL) was stirred at 70° C. for 2 h. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:9 to 1:1) to give a yellow amorphous solid. A mixture of the solid, ethyl 2-butynoate (0.78 g), tributylphosphine (565 mg) and tetrahydrofuran (50 mL) was refluxed for 15 h, and then ethyl 2-butynoate (0.78 g) and tributylphosphine (565 mg) were added to the mixture. The whole was refluxed for further 30 min, and then concentrated in vacuo. The residue was purified by basic silica gel chromatography (ethyl acetate:hexane=1:9 to 1:1, volume ratio) and then by silica gel chromatography (ethyl acetate:hexane=1:9 to 2:1) to give the title compound (0.68 g, 50%) as a yellow oil. MS 484 (MH+).

Provenance & Evidence