反应详情

A mixture of 4-bromobenzaldehyde (2.78 g; 15.0 mmol), [3-(aminocarbonyl)-phenyl]boronic acid (2.72 g; 16.5 mmol), PdCl2(dppf).CH2Cl2 (0.306 g; 0.38 mmol), DME (25 mL) and Na2CO3 (25 mL of a 2M solution) was sparged 20 min with N2 and heated under reflux for 90 min (consumption of aryl bromide observed by LC/MS). Upon cooling, the mixture was partitioned between EtOAc/H2O, layers were separated, and the aqueous layer was extracted with EtOAc (×2). Combined organics were washed (H2O, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a tan solid. LC/MS (method A) 1.91 min, m/z 226 (M+H).

1. temperatureheated
2. temperatureunder reflux for 90 min
3. custom(consumption of aryl bromide observed by LC/MS)
4. temperatureUpon cooling
5. customthe mixture was partitioned between EtOAc/H2O, layers
6. customwere separated
7. extractionthe aqueous layer was extracted with EtOAc (×2)
8. washCombined organics were washed (H2O, brine)
9. dry with materialdried over Na2SO4
10. concentrationconcentrated in vacuo
11. customThe residue was purified by flash chromatography (EtOAc/hexanes)