反应详情

A mixture of 4-(2-morpholin-4-yl-ethoxy)-phenylamine (1.4 g, 6.2 mmol), 3-iodophthalic acid dimethyl ester (2.0 g, 6.2 mmol), Pd2(dba)3 (0.26 g, 0.28 mmol), rac-BINAP (0.12 g, 0.19 mmol), and cesium carbonate (2.8 g, 8.6 mmol), in 12 mL toluene was heated to reflux under nitrogen for 16 hours. The reaction mixture was cooled, diluted with CH2Cl2 (20 mL), and filtered through Celite, and the filter was washed with additional CH2Cl2 (60 mL). The filtrate was evaporated in vacuo, and the residue was purified by ISCO silica gel flash chromatography using a methylene chloride-methanol gradient, eluting 1.8 g of the product at 95:5 methylene chloride-methanol, in 70% yield, as a pale yellow solid; 1H NMR (CDCl3) δ 3.00-3.51 (m, 6H), 3.87 (s, 3H), 3.88 (s, 3H), 4.08-4.34 (m, 4H), 4.52-4.62 (m, 2H), 6.89 (d, J=8.7 Hz, 2H), 6.99 (d, J=7.1, 1H), 7.09-7.12 (m, 3H), 7.23-7.28 (m, 1H), 8.08 (s, 1H).

1. temperatureto reflux under nitrogen for 16 hours
2. temperatureThe reaction mixture was cooled
3. filtrationfiltered through Celite
4. washthe filter was washed with additional CH2Cl2 (60 mL)
5. customThe filtrate was evaporated in vacuo
6. customthe residue was purified by ISCO silica gel flash chromatography
7. washeluting 1.8 g of the product at 95:5 methylene chloride-methanol