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

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).

1. temperatureto reflux under nitrogen for 24 hours
2. temperatureThe reaction mixture was cooled
3. filtrationfiltered through Celite
4. washthe filter was washed with additional CH2Cl2 (30 mL)
5. customThe filtrate was evaporated
6. customthe residue was chromatographed
7. washeluting 0.9 g of the product at 92:8 methylene chloride-methanol

ORD record

ord-2415a64aa76940e5a73a138c21a5bfbd

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481568B2