反应详情

温度

22.5 °C

A mixture of methyl-3-bromo-5-[(dipropylamino)carbonyl]benzoate (XLVIII, 200 mg, 0.58 mmol), 8-quinolineboronic acid (200.6 mg, 1.2 mmol), sodium carbonate (870 Micro Liter of a 2 M mixture in water, 1.74 mmol) in toluene (6 mL) is degassed under reduced pressure for 15 minutes and purged with argon. Palladium tetrakis(triphenylphosphine) (139 mg, 0.12 mmol) is added and the reaction mixture is degassed under reduced pressure for 15 minutes and purged with argon. The reaction mixture is heated at reflux overnight, cooled to 20-25 degrees C. and diluted with chloroform. The organic phase is separated and washed with water (3×50 mL), and saline, dried over sodium sulfate and concentrated under reduced pressure. Purification by flash column chromatography (silica, ethyl acetate/hexanes, 1.3/1) gives methyl 3-[(dipropylamino)carbonyl]-5-(8-quinolinyl)benzoate (XLIX, 176 mg), NMR (300 MHz, CDCl3): delta 8.91, 8.42, 8.21, 8.09, 7.95, 7.86, 7.77, 7.64, 3.94, 3.49, 3.34, 1.64, 0.99 and 0.84.

1. customis degassed under reduced pressure for 15 minutes
2. custompurged with argon
3. customthe reaction mixture is degassed under reduced pressure for 15 minutes
4. custompurged with argon
5. temperatureThe reaction mixture is heated
6. temperatureat reflux overnight
7. additionand diluted with chloroform
8. customThe organic phase is separated
9. washwashed with water (3×50 mL), and saline
10. dry with materialdried over sodium sulfate
11. concentrationconcentrated under reduced pressure
12. customPurification by flash column chromatography (silica, ethyl acetate/hexanes, 1.3/1)