Cesium carbonate → 3-[3-(2-Morpholin-4-yl-ethoxy)-phenylamino]-phthalic acid dimethyl ester

Participants

Reaction Steps

A mixture of 3-(2-morpholin-4-yl-ethoxy)-phenylamine (1.4 g, 6.1 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 1.9 g of the product at 95:5 methylene chloride-methanol, in 73% yield; 1H NMR (CDCl3) δ 2.57 (t, J=4.6 Hz, 4H), 2.79 (t, J=5.7 Hz, 2H), 3.73 (t, J=4.6 Hz, 4H), 3.87 (s, 3H), 3.89 (s, 3H), 4.09 (t, J=5.7 Hz, 2H), 6.60 (dd, J=8.0 Hz, J=2.0 Hz, 1H), 6.70 (t, J=2.1 Hz, 1H), 6.74 (dd, J=7.8 Hz, J=1.8 Hz, 1H), 7.11 (dd, J=7.4 Hz, J=1.0 Hz, 1H), 7.21 (t, J=8.1 Hz, 1H), 7.31 (t, J=8.0 Hz, 1H), 7.43 (dd, J=8.4 Hz, J=0.9 Hz, 1H), 7.98 (s, 1H).

Provenance & Evidence