反应详情

温度

65 °C

To a mixture of 3-(5-bromo-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (467 mg, 1.42 mmol), 1-dimethylamino-2-propyne (473 mg, 5.69 mmol), copper(I) iodide (48 mg, 0.25 mmol), triethylamine (287 mg, 2.84 mmol) in DMF (5 ml), was added tetrakis(triphenylphosphine)palladium (100 mg, 0.086 mmol). The mixture was heated at 65° C. under argon for 16 hours, and then cooled to room temperature. The mixture was diluted with MeOH (100 ml). The insoluble material was removed by filtration, and the filtrate solution was concentrated and then diluted with EtOAc (200 ml). The resulting mixture was washed with brine (3×100 ml), dried over anhydrous Na2SO4, and concentrated to give a dark-brown residue. Purification of the residue by silica gel column chromatography, eluted with a gradient of MeOH in CHCl3, afforded 3-[5-(3-dimethylamino-prop-1-ynyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a brown solid (320 mg, 68%).

1. temperaturecooled to room temperature
2. customThe insoluble material was removed by filtration
3. concentrationthe filtrate solution was concentrated
4. additiondiluted with EtOAc (200 ml)
5. washThe resulting mixture was washed with brine (3×100 ml)
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated
8. customto give a dark-brown residue
9. customPurification of the residue by silica gel column chromatography
10. washeluted with a gradient of MeOH in CHCl3