反应详情

To a solution of (3-{[2-(2-bromo-phenylamino)-ethylamino]-methyl}-phenyl)-piperidin-1-yl-methanone (Example 17; 0.051 g, 0.12 mmol) and 2-methoxybenzeneboronic acid (0.037 g, 0.25 mmol) in 2 M Na2CO3/EtOH/toluene (1:1:4, 6 mL) was added Pd(PPh3)4(0.014 g, 0.012 mmol), and the resulting solution was stirred at reflux for 16 h. The solution was partitioned with EtOAc (20 mL) and satd aqueous NaHCO3 (20 mL), and the aqueous layer was back-extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by preparative TLC (10% CH3OH/CH2Cl2) to provide a tan oil (0.0168 g, 28%). MS (ESI): mass calculated for C28H33N3O2, 443.26. m/z found, 444.2 [M+H]+, 466.2 [M+Na]+. 1H NMR (400 MHz, CDCl3): 7.38-7.22 (m, 7H), 7.08-6.97 (m, 3H), 6.78-6.72 (br s, 2H), 4.15 (br s, 1H), 3.69-3.76 (br m, 4H), 3.68 (s, 3H), 3.29-3.24 (br m, 4H), 2.86-2.76 (m, 2H), 1.75-1.49 (br m, 8H). 13C NMR (100 MHz, CDCl3): 170.2, 156.8, 145.8, 140.4, 136.5, 131.9, 130.7, 129.0, 128.9, 128.6, 128.4, 128.0, 126.4, 125.3, 124.9, 121.1, 116.8, 111.2, 110.5, 55.6, 53.2, 48.7, 47.8, 43.5, 43.6, 26.5, 25.6, 24.5.

1. temperatureat reflux for 16 h
2. customThe solution was partitioned with EtOAc (20 mL)
3. extractionthe aqueous layer was back-extracted with EtOAc (3×30 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude residue was purified by preparative TLC (10% CH3OH/CH2Cl2)