反应详情

温度

150 °C

To a microwave vial, 3-(4-bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (50 mg, 0.121 mmol) was dissolved in DMF (2 ml) and triethyl amine (0.506 ml, 3.63 mmol). To the solution was added the 4-vinyl-1-methyl imidazole (39.2 mg, 0.363 mmol) and Pd(PPh3)2Cl2 (8.49 mg, 0.012 mmol). The system was flushed with nitrogen and heated at 150° C. for 1 h under microwave radiation. The mixture was cooled to room temperature and diluted with DCM and sat. NH4Cl. The organic layer was collected (phase separator) and purified by reverse phase HPLC (acidic condition, 0.1% TFA in 1-100% CH3CN/H2O) to afford (E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-imidazol-4-yl)vinyl)phenoxy)benzo[b]thiophen-6-ol (31 mg, 0.070 mmol, 58.2% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm=3.82 (s, 3 H) 6.57-6.74 (m, 3 H) 6.75-6.93 (m, 3 H) 6.98-7.14 (m, 3 H) 7.32-7.54 (m, 5 H) 8.73 (s, 1 H), LC/MS (m/z, MH+): 441.3.

1. customThe system was flushed with nitrogen
2. temperatureThe mixture was cooled to room temperature
3. additiondiluted with DCM and sat. NH4Cl
4. customThe organic layer was collected (phase separator)
5. custompurified by reverse phase HPLC (acidic condition, 0.1% TFA in 1-100% CH3CN/H2O)