反应详情

A solution of 5-benzylbenzofuran-2-ylboronic acid (252 mg, 1.0 mmole) in ethanol (3 ml) was added to a mixture of 1-(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone and 1-(8-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone (308 mg, 1.0 mmole), Pd(PPh3)4, toluene, and 2 M Na2CO3(3.5 ml). The resulting mixture was heated at reflux overnight. The reaction was concentrated in vacuo, and the residue was diluted with water. The aqueous phase was extracted with EtOAc (3×50 ml). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified on ISCO column (5% to 10% MeOH/CH2Cl2) to provide the title compounds (189 mg, 56%). 1H NMR (400 MHz, CDCl3) δ 7.60 (m, 2H), 7.39 (dd, 1H), 7.37 (s, 1H), 7.25 (m, 5H), 7.10 (dd, 2H), 6.90 (s, 1H), 4.10 (s, 2H), 3.40 (s, 2H), 3.18 (m, 2H), 2.94 (m, 2H). MS (ESI) m/z: Calculated: 339.16; Observed: 340.10 (M++1).

1. temperatureThe resulting mixture was heated
2. temperatureat reflux overnight
3. concentrationThe reaction was concentrated in vacuo
4. additionthe residue was diluted with water
5. extractionThe aqueous phase was extracted with EtOAc (3×50 ml)
6. washThe combined organic phases were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified on ISCO column (5% to 10% MeOH/CH2Cl2)