反应详情

温度

0 °C

1,1-Dimethylethyl 7-(methyloxy)-1-oxo-1,2,3,4-tetrahydro-9H-β-carboline-9-carboxylate (0.075 g, 0.23 mmol) was dissolved in THF (2 mL) and cooled to 0° C. Sodium hydride (60% dispersion in oil, 0.01 g, 0.25 mmol) was added and the mixture was stirred for 15 min. 3-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.09 g, 0.23 mmol) was added. The reaction mixture was allowed to warm to RT and stirred for 1 h. 10% Aqueous citric acid and EtOAc were added. The layers were separated and the aqueous layer extracted with EtOAc (3×5 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated. Purification was accomplished by column chromatography (hexane/EtOAc) to afford the title compound (0.034 g, 24%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.83 (s, 1H), 7.81 (d, 1H), 7.52 (d, 1H), 7.45-7.51 (m, 2H), 7.34 (t, 1H), 7.20 (d, 1H), 7.07 (dd, 1H), 4.79 (s, 2H), 3.79 (s, 3H), 3.71 (t, 2H), 2.94 (t, 2H), 1.48 (s, 9H). MS: m/z 632.2 (M+23).

1. temperatureto warm to RT
2. stirringstirred for 1 h
3. customThe layers were separated
4. extractionthe aqueous layer extracted with EtOAc (3×5 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customevaporated
8. customPurification