反应详情

Zinc (100 g, 1.54 mol) was added to a solution of 3,3-dibromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-h]pyridin-2-one from Step B (65 g, 0.154 mol) in THF (880 mL) and saturated aqueous ammonium chloride (220 mL). After 3 h, the reaction was filtered and concentrated in vacuo. The residue was partitioned between EtOAc and H2O which resulted in the formation of a white precipitate. Both layers were filtered through a Celite pad and the layers were separated. The aqueous layer was washed with EtOAc (2×) and the combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated. The crude product was filtered through a plug of silica gel eluting with CH2Cl2:EtOAc—90:10 and the eluant was concentrated under reduced pressure to provide the title compound. MS: m/z=265 (M+1).

1. filtrationthe reaction was filtered
2. concentrationconcentrated in vacuo
3. customThe residue was partitioned between EtOAc and H2O which
4. customresulted in the formation of a white precipitate
5. filtrationBoth layers were filtered through a Celite pad
6. customthe layers were separated
7. washThe aqueous layer was washed with EtOAc (2×)
8. washthe combined organic layers were washed with H2O
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. filtrationThe crude product was filtered through a plug of silica gel eluting with CH2Cl2
13. concentrationEtOAc—90:10 and the eluant was concentrated under reduced pressure