反应详情

To a solution of 1,2-bis(bromomethyl)-4-nitrobenzene (40.9 g, 132 mmol, described in Intermediate 2) and 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (31.5 g, 119 mmol, described in Intermediate 1) in DMF (2 L) was added cesium carbonate (129 g, 397 mmol), portionwise, over 5 min. After 18 h, acetic acid (7.6 mL) was added and the mixture was concentrated to a volume of about 500 mL, then partitioned between EtOAc (1.5 L) and H2O (1 L). The organic layer was washed with H2O (1 L), then brine (500 mL), then dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-100:0 to 0:100, to give the title compound. MS: m/z=412 (M+1).

1. waitAfter 18 h
2. concentrationthe mixture was concentrated to a volume of about 500 mL
3. custompartitioned between EtOAc (1.5 L) and H2O (1 L)
4. washThe organic layer was washed with H2O (1 L)
5. dry with materialbrine (500 mL), then dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by silica gel chromatography
9. washeluting with a gradient of hexane