反应详情

A mixture of 4-(2,4-dichloro-5-methoxyanilino)-7-iodo-6-methoxy-3-quinolinecarbonitrile (3.5 g, 7.00 mmol), tributyl [5-(diethoxymethyl)-3-furanyl]stannane (generated from reaction of 4-bromo-2-(diethoxymethyl)-furan [ref. Chiarello, J, Joullie, M. M., Tetrahedron, 44(1), 41-48 (1988)] with tributyl tin chloride in the presence of n-BuLi) (5.76 g, 12.55 mmol), and dichlorobis(triphenylphosphine)pallidium (II) (100 mg) in 80 mL of dioxane is heated at reflux for 5 hours. Additional dichlorobis(triphenylphosphine)pallidium (II) (100 mg) is added and the reaction mixture is heated at reflux overnight. The reaction mixture is partitioned between ethyl acetate and water. The insoluble material is collected by filtration to provide 1.09 g of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-[5-(diethoxymethyl)-3-furyl]-6-methoxy-3-quinolinecarbonitrile as a pale green solid; 1H NMR (DMSO-d6) δ 1.18 (t, J=7 Hz, 6H), 3.63 (q, J=7 Hz, 4H), 3.87 (s, 3H), 4.07 (s, 3H), 5.60 (s, 1H), 7.13 (s, 1H), 7.37 (s, 1H), 7.76 (s, 1H), 7.95 (s, 1H), 8.15 (s, 1H), 8.35 (s, 1H), 8.45 (s, 1H), 9.84 (s, 1H); MS 542.1, 544.1 (M+H)+.

1. temperatureis heated
2. temperatureat reflux for 5 hours
3. temperaturethe reaction mixture is heated
4. temperatureat reflux overnight
5. customThe reaction mixture is partitioned between ethyl acetate and water
6. filtrationThe insoluble material is collected by filtration