反应详情

温度

70 °C

Add cesium carbonate (186.6 g, 572.7 mmol), (2-bromoethoxy)-tert-butyldimethylsilane (88.0 mL, 409.1 mmol), and sodium iodide (6.1 g, 40.9 mmol) to a suspension of 5,7-dihydropyrido[2,3-d][3]benzazepin-6-one (86.0 g, 409.1 mmol) in dimethylformamide (860 mL) and stir at 70° C. for 20 hours. Cool mixture to ambient temperature, pour over ice and water (100 mL), add ethyl acetate (200 mL). Filter mixture through Celite®, then wash with ethyl acetate (100 mL). Separate layers of filtrate, extract from aqueous with ethyl acetate (2×50 mL). Wash combined organics with water (2×100 mL), brine (100 mL), dry over sodium sulfate and concentrate. Dissolve material in tetrahydrofuran (1.28 L), add Silia® bond palladium scavenger (16.7 g) and stir at ambient temperature for 20 hours. Filter through a pad of silica, wash with tetrahydrofuran (200 mL) and concentrate to obtain the title compound (155 g, 420.6 mmol) as a light brown oil that crystallizes in quantitative yield. MS (m/z): 369 (M+1).

1. temperatureCool mixture to ambient temperature
2. filtrationFilter mixture through Celite®
3. washwash with ethyl acetate (100 mL)
4. extractionSeparate layers of filtrate, extract from aqueous with ethyl acetate (2×50 mL)
5. washWash
6. dry with materialdry over sodium sulfate
7. concentrationconcentrate
8. additionDissolve material in tetrahydrofuran (1.28 L), add Silia® bond palladium scavenger (16.7 g)
9. stirringstir at ambient temperature for 20 hours
10. filtrationFilter through a pad of silica
11. washwash with tetrahydrofuran (200 mL)
12. concentrationconcentrate