反应详情

温度

80 °C

A mixture of 4-bromo-1-(tris(4-methoxyphenyl)methyl)-1H-pyrazole (1.47 g, 3.1 mmol), (4-formylphenyl)boronic acid (0.94 g, 6.3 mmol), and K2CO3 (0.65 g, 4.7 mmol) in DME-H2O (25 mL, 4:1) was degassed by alternately putting under house vacuum and argon three times for several minutes each. Tetrakis(triphenylphosphine)palladium (0.35 g, 0.3 mmol) was added then the mixture was degassed again. After heating for 16.5 hrs at 80° C. and cooling to room temperature, H2O was added. The mixture was extracted with EtOAc and the combined organics were washed with H2O, saturated aqueous NaHCO3 and brine then dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (20-30% EtOAc-hexanes; EtOAc containing 1% Et3N) gave 4-(1-(tris(4-methoxyphenyl)methyl)-1H-pyrazol-4-yl)benzaldehyde (1.31 g combined from two reactions, 33%).

1. customwas degassed
2. waitby alternately putting under house vacuum and argon three times for several minutes
3. customthe mixture was degassed again
4. temperaturecooling to room temperature
5. additionH2O was added
6. extractionThe mixture was extracted with EtOAc
7. washthe combined organics were washed with H2O, saturated aqueous NaHCO3 and brine
8. dry with materialthen dried over Na2SO4
9. concentrationconcentrated in vacuo
10. customPurification by chromatography (20-30% EtOAc-hexanes; EtOAc containing 1% Et3N)