反应详情

A stirred solution of 4-(4-methoxyphenyl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one (500 mg, 1.18 mmol) in 2N methanolic MeNH2 (50 mL) was refluxed for 3 h. The reaction mixture was then concentrated in vacuo and the residue was dissolved in 4N HCl in dioxane The reaction mixture was refluxed for 16 h, then basified with aqueous NaHCO3 solution and extracted with EtOAc (2×30 mL). The combined organic layers were washed with water, dried over Na2SO4, filtered, and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 4-(4-methoxyphenyl)-1-methyl-3-(4-(quinolin-2-ylmethoxy)phenyl)-1H-pyrrol-2(5H)-one (150 mg, 29%) as a solid. 1H NMR (500 MHz, d6-DMSO): δ 8.43-8.39 (m, 1H), 8.04-7.98 (m, 2H), 7.82-7.56 (m, 3H), 7.18-7.09 (m, 4H), 7.04 (d, J=7.2 Hz, 2H), 6.82 (d, J=7.2 Hz, 2H), 5.39 (s, 2H), 4.38 (s, 2H), 3.78 (s, 3H), 2.99 (s, 3H). MS: M+H: m/z=437.1; M+Na: m/z=459.2; M+K: m/z=475.2 and HPLC: 87%, (Condition-B).

1. concentrationThe reaction mixture was then concentrated in vacuo
2. dissolutionthe residue was dissolved in 4N HCl in dioxane The reaction mixture
3. temperaturewas refluxed for 16 h
4. extractionextracted with EtOAc (2×30 mL)
5. washThe combined organic layers were washed with water
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto obtain the crude product
10. customThe crude material was purified via silica gel column chromatography