Cesium carbonate → 3-(4-Dimethylaminomethyl-2-methoxyphenylamino)phthalic acid dimethyl ester

Participants

Reaction Steps

A mixture of 3-iodophthalic acid dimethyl ester (1.0 g, 3.1 mmol), 4-dimethylaminomethyl-2-methoxyphenylamine (0.56 g, 3.1 mmol), Pd2(dba)3 (0.13 g, 0.14 mmol), rac-BINAP (0.058 g, 0.093 mmol), and cesium carbonate (1.4 g, 4.3 mmol), in 6 mL toluene was heated to reflux under nitrogen for 24 hours. The reaction mixture was cooled, diluted with CH2Cl2 (10 mL), and filtered through Celite, and the filter was washed with additional CH2Cl2 (30 mL). The filtrate was evaporated, and the residue was chromatographed using a methylene chloride-methanol gradient, eluting 0.9 g of the product at 92:8 methylene chloride-methanol, in 78% yield: 1H NMR (CDCl3) δ 2.31 (s, 6H), 3.47 (s, 2H), 3.87 (s, 3H), 3.88 (s, 3H), 3.90 (s, 3H), 6.80 (dd, J=8.0 Hz, J=1.4 Hz, 1H), 6.99 (s, 1H), 7.14 (dd, J=7.3 Hz, J=0.9 Hz, 1H), 7.20 (d, J=8.0 Hz, 1H), 7.31 (t, J=7.9 Hz, 1H), 7.45 (dd, J=8.5 Hz, J=0.9 Hz, 1H), 7.99 (br, 1H).

Provenance & Evidence