反应详情

A dry nitrogen-purged flask was charged with 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phospha-bicyclo[3.3.3]undecane (38 mg, 0.111 mmol), tris(dibenzylideneacetone)-dipalladium (25.4 mg, 0.0277 mmol), and sodium tert-butoxide (82.4 mg, 0.8322 mmol). A solution of the product of Example 5G (118 mg, 0.5548 mmol) in anhydrous toluene (2 mL) and a solution of the product from Example 5I (107.5 mg, 0.4993 mmol) in toluene (3 mL) were added via syringe. The reaction was heated at reflux in a preheated 120° oil bath for 18 hours, cooled to room temperature, treated with additional tris(dibenzylideneacetone)dipalladium (25.4 mg), and heated at reflux for an additional 2.5 hours. The reaction was cooled to room temperature and the solvent removed by rotary evaporation in vacuo. Purification by silica gel flash chromatography with a gradient of 1% to 3% ethyl acetate/methylene chloride afforded the title compound (29 mg, 0.074 mmol, 15%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.00 (t, J=7.35 Hz, 3H) 1.71-1.90 (m, 2H) 2.38 (s, 3H) 3.05 (t, J=7.35 Hz, 2H) 6.87 (d, J=5.52 Hz, 1H) 7.07 (dd, J=7.91, 1.29 Hz, 1H) 7.12-7.31 (m, 5H) 7.37-7.46 (m, 2H) 8.15 (d, J=5.52 Hz, 1H) 8.52 (s, 1H); MS (DCI/NH3) m/z 392 (M+H)+.

1. customA dry nitrogen-purged flask
2. temperatureThe reaction was heated
3. temperatureat reflux in a preheated 120° oil bath for 18 hours
4. temperatureheated
5. temperatureat reflux for an additional 2.5 hours
6. temperatureThe reaction was cooled to room temperature
7. customthe solvent removed by rotary evaporation in vacuo
8. customPurification by silica gel flash chromatography with a gradient of 1% to 3% ethyl acetate/methylene chloride