反应详情

温度

120 °C

To a solution of methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (80 mg, 0.4 mmol) and p-bromoanisole (73.9 μL, 0.6 mmol) in dimethyl sulfoxide (2 mL) was added L-proline (18 mg, 0.16 mmol), potassium carbonate (0.11 g, 0.79 mmol) and copper(I) iodide (15 mg, 0.079 mmol). The reaction mixture was heated to 120° C. and stirred overnight. The mixture was then cooled to rt, water added and extracted with DCM (15 mL, 3×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was purified by flash silica gel chromatography (0% to 50% EtOAc/hexanes) to afford methyl 2-(4-methoxyphenyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (30 mg, 20%). LC-MS: (FA) ES+ 310.

1. temperatureThe mixture was then cooled to rt
2. extractionextracted with DCM (15 mL, 3×)
3. washThe combined organic phases were then washed with water, and brine
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude residue was purified by flash silica gel chromatography (0% to 50% EtOAc/hexanes)