反应详情

温度

100 °C

Compound 11 (106 mg, 0.43 mmol) and copper (I) iodide (1.6 mg, 2 mol %) were added to an oven-dried reaction flask containing toluene (2 mL) and Et3N (2 mL). The reaction mixture was stirred at room temperature for 5 min with N2 (g) bubbling. Bis(triphenylphosphine)palladium(II) dichloride (3 mg, 1 mol %) and a solution of compound 8 (63 mg, 0.43 mmol) in Et3N (1 mL) were added. The reaction mixture was stirred at 100° C. for 24 h. The reaction was cooled to room temperature, then diluted with EtOAc (50 mL) and washed with brine (3×20 mL). The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (20% EtOAc in hexanes) to afford compound 12 in 62.8% (84 mg) yield as a brown solid. 1H-NMR (CDCl3, 400 MHz) δ 8.00 (1H, d, J=8.4 Hz, Ar), 7.14 (1H, s, Ar), 6.93 (1H, d, J=1.6 Hz, Ar), 6.88 (1H, dd, J=8.4 Hz, 1.6 Hz, Ar), 6.81 (1H, dd, J=8.4 Hz, 1.6 Hz, Ar), 6.68 (1H, d, J=8.4 Hz, Ar), 4.79 (2H, s, NH2), 3.89 (6H, s, 2×OCH3), 3.76 (3H, s, OCH3); 13C-NMR (CDCl3, 100 MHz) δ 165.9, 162.3, 151.4, 144.5, 132.8, 126.6, 122.9, 118.5, 117.9, 115.8, 115.6, 114.4, 107.6, 93.9, 92.6, 56.0, 55.7, 52.2; MS (ESI) m/z Calcd for C18H17NO4 (M+): 311.1, Found: 312.0 (M+H+).

1. custombubbling
2. temperatureThe reaction was cooled to room temperature
3. washwashed with brine (3×20 mL)
4. customThe organic layer was collected
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. custompurified by silica column chromatography (20% EtOAc in hexanes)