反应详情

To a stirred solution of 3-bromo-4-morpholinofuran-2(5H)-one (300 mg, 1.20 mmol) in 2:1 toluene/H2O (8 mL) were added 2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl)quinoline (480 mg, 1.33 mmol), Cs2CO3 (1.54 g, 4.23 mmol) and Pd(dppf)Cl2 (197.5 mg, 0.24 mmol). The reaction mixture was then refluxed for 4 h, filtered and the filtrate was partitioned between water and EtOAc. The organic layer was separated, washed with water, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude material was purified via silica gel column chromatography eluting with 40% EtOAc in hexanes to afford 4-morpholino-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one (50 mg, 10%) as a solid. 1H NMR (500 MHz, d6-DMSO): δ 8.42 (d, J=7.6 Hz, 1H), 8.04-7.96 (m, 2H), 7.82-7.76 (m, 1H), 7.70-7.67 (m, 1H), 7.65-7.59 (m, 1H), 7.17 (d, J=7.2 Hz, 2H), 7.05 (d, J=7.2 Hz, 2H), 5.38 (s, 2H), 4.91 (s, 2H), 3.60 (bs, 4H), 3.19 (bs, 4H). MS: M+H: m/z=403.1; M+Na: m/z=425.2 HPLC: 90%, (Condition-J).

1. temperatureThe reaction mixture was then refluxed for 4 h
2. filtrationfiltered
3. customthe filtrate was partitioned between water and EtOAc
4. customThe organic layer was separated
5. washwashed with water
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude material was purified via silica gel column chromatography
10. washeluting with 40% EtOAc in hexanes