反应详情

温度

160 °C

A mixture of 9-bromo-5-methoxycarbonylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (530 mg, 1.50 mmol), potassium iodide (4.98 g, 30 mmol) and cuprous iodide (2.0 g, 10.5 mmol) in hexamethylphosphoric triamide (5 mL) was heated at 160° C. for 6.5 h and poured into 1N aqueous ammonium chloride (200 mL). The mixture was extracted with a mixed solvent of THF and ethyl acetate (600 mL). The extract was washed with 1N aqueous ammonium chloride (200 mL×2) and brine (200 mL), dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 0.7 to 1% acetic acid/ethyl acetate to give 465 mg of the title compound (78%): mp 241°~243° C.; 1H NMR (270 MHz, DMSO-d6) δ12.01 (bs, 1H), 7.33 (s, 1H), 7.31 (s, 1H), 5.03~5.14 (m, 1H), 3.62 (s, 3H), 2.93 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.78 (dm, 1H, J=17.1 Hz), 2.54~2.69 (m, 2H), 2.09 (dm, 1H, J=13.5 Hz), 1.79~1.96 (m, 1H).

1. extractionThe mixture was extracted with a mixed solvent of THF and ethyl acetate (600 mL)
2. washThe extract was washed with 1N aqueous ammonium chloride (200 mL×2) and brine (200 mL)
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated
5. customThe residue was purified by silica gel column chromatography with 0.7 to 1% acetic acid/ethyl acetate