反应详情

To a suspension of 2 (0.1065 g, 0.424 mmol) in 20 mL toluene/10 mL EtOH was added phenylboronic acid (0.08 g, 0.636 mmol), Na2CO3 (0.113 g, 1.06 mmol) dissolved in a minimum amount of water, LiCl (0.054 g, 1.27 mmol), and tetrakis(triphenylphosphine)palladium(0) (24.5 mg, 21.0 μmol). The reaction mixture was refluxed for 16 h. The solvent was removed in vacuo, and the residue was taken up in EtOAc and washed with saturated aqueous NaHCO3, H2O, and brine. The organic layer was dried over Na2SO4 and concentrated to give a yellow solid, which was purified by flash column chromatography eluting with a gradient of 20% of EtOAc in hexanes to give 0.098 g of a mixture of 3 as a yellow solid. mp 215-218° C. (dec); 1H NMR (DMSO-d6) δ 5.04 (s, 2H), 7.17 (t, 1H, J=7.5 Hz), 7.34 (d, 1H, J=6.6 Hz), 7.35 (d, 1H, J=7.4 Hz), 7.50 (m, 4H), 7.66 (d, 1H, J=7.7 Hz), 7.84 (s, 1H), 11.64 (s, 1H); HRMS (M+H) 249.1023.

1. temperatureThe reaction mixture was refluxed for 16 h
2. customThe solvent was removed in vacuo
3. washwashed with saturated aqueous NaHCO3, H2O, and brine
4. dry with materialThe organic layer was dried over Na2SO4
5. concentrationconcentrated
6. customto give a yellow solid, which
7. customwas purified by flash column chromatography
8. washeluting with a gradient of 20% of EtOAc in hexanes