反应详情

温度

80 °C

A flask charged with 3-(2-morpholin-4-ylethyloxy)iodobenzene (0.33 g, 1 mmol), bis(pinacolato)diboron (0.279 g, 1.1 mmol), potassium acetate (0.294 g, 3 mmol) and PdCl2(dppf) (48 mg, 0.06 mmol) was flushed with nitrogen. N,N-Dimethylformamide (6 mL) was added and the reaction mixture was stirred at 80° C. for 3h and then cooled to room temperature. 3-Bromo-4-(1-methylindol-3-yl)-1-methylpyrrole-2,5-dione (0.255 g, 0.8 mmol) ((synthesized according to the procedures described in Brenner, M. et al., Tet. Lett. 44, 2887, (1988)) was added to the reaction mixture, followed by the addition of PdCl2(dppf) (48 mg, 0.06 mmol)) and 2M aq. Na2CO3 (2.5 mL). The resulting mixture was stirred at 80° C. for 2.5 h, then cooled to room temperature, and quenched with H2O. The product was extracted with EtOAc. The EtOAc layer was washed with H2O, NaCl (sat.), dried over Na2SO4, and concentrated. Purification of the crude product on a silica gel column with 2/3/5 of acetone/CH2Cl2/hexane gave 3-(1-methylindol-3-yl)-4-[3-(2-morpholin-4-ylethyloxy)-phenyl]-1-methylpyrrole-2,5-dione as an orange-red oil. (0.25 g, 70% yield).

1. customwas flushed with nitrogen
2. additionN,N-Dimethylformamide (6 mL) was added
3. temperaturecooled to room temperature
4. addition44, 2887, (1988)) was added to the reaction mixture
5. stirringThe resulting mixture was stirred at 80° C. for 2.5 h
6. temperaturecooled to room temperature
7. customquenched with H2O
8. extractionThe product was extracted with EtOAc
9. washThe EtOAc layer was washed with H2O, NaCl (sat.)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated
12. customPurification of the crude product on a silica gel column with 2/3/5 of acetone/CH2Cl2/hexane