反应详情

To a mixture of (7-fluoro-quinolin-6-yl)-acetic acid methyl ester (14.0 g, 63.9 mmol) and pyridine (10.4 mL, 127.8 mmol) in 200 mL of carbon tetrachloride was added bromine (6.6 mL, 127.8 mmol) in a dropwise fashion. The mixture was heated to reflux for 2 hrs before being cooled to ambient temperature. The liquid in the flask was decanted and washed with NaHCO3 and water. The dark solid on the bottom of the flask was treated with NaHCO3 and dichloromethane. The combined organic layers were washed with water, dried (Na2SO4) and evaporated to dryness. The crude product was purified via flash column chromatography eluting with petroleum ether/ethyl acetate (40/1˜3/1) to return 13.9 g (75% yield) of the title compound as white crystalline solid. 1H NMR (DMSO-d6): δ 8.89 (s, 1H), 8.27 (m, 1H), 7.66˜7.74 (m, 2H), 3.87 (s, 2H), 3.74 (s, 3H).

1. temperatureThe mixture was heated
2. temperatureto reflux for 2 hrs
3. customThe liquid in the flask was decanted
4. washwashed with NaHCO3 and water
5. additionThe dark solid on the bottom of the flask was treated with NaHCO3 and dichloromethane
6. washThe combined organic layers were washed with water
7. dry with materialdried (Na2SO4)
8. customevaporated to dryness
9. customThe crude product was purified via flash column chromatography
10. washeluting with petroleum ether/ethyl acetate (40/1˜3/1)