反应详情

A mixture of 1,1-dimethylethyl {2-[(4-bromophenyl)oxy]ethyl}(4,4-dimethylcyclohexyl)carbamate (0.085 g; 0.20 mmol; Example V-8), [4-(acetylamino)phenyl]boronic acid (0.040 g; 0.22 mmol), PdCl2(dppf).CH2Cl2 (0.005 g; 0.006 mmol), Na2CO3 (2 mL of a 2M solution) and DME (2 mL) was sparged with N2 for 10 minutes at room temperature and heated at 80° for 1 h (until consumption of the aryl bromide, as judged 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 (brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a pale yellow solid. LC/MS (method A) tR 3.29 min, m/z 481 (M+H, 53%), 381 ([M−Boc]+H, 100%).

1. temperatureheated at 80° for 1 h (
2. customuntil consumption of the aryl bromide
3. temperatureUpon cooling
4. customthe mixture was partitioned between EtOAc/H2O, layers
5. customwere separated
6. extractionthe aqueous layer was extracted with EtOAc (×2)
7. washCombined organics were washed (brine)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue was purified by flash chromatography (EtOAc/hexanes)