反应详情

To a stirred solution of 7-chloro-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (123.5 g, 565 mmol) in DMF (941 ml) was added NBS (111 g, 621 mmol) in one portion at 5° C. The reaction exothermed. When the exotherm subsided, the ice bath was removed and the reaction was agitated at ambient temp for 40 min. The reaction mixture was poured into water (2 L) and the precipitate was filtered and washed with water. The cake was slurried in MeOH (4 L), heated to 65° C. for 1 h, and filtered through a fritted glass. The filtrate was treated with activated charcoal, heated to 65° C. for 1 h, filtered through a pad of Celite, washed with hot MeOH (2 L), and concentrated until the volume became about 300 mL. The residue was cooled to 0° C., and the precipitate was filtered, washed with MTBE, and dried to give the title compound. 1H NMR (600 MHz, CD3SOCD3) δ 12.11 (s, 1H); 11.54 (s, 1H); 8.07 (d, 1H); 7.63 (s, 1H); 7.55 (d, 1H); 7.27 (dd, 1H). LRMS (APCI) calc'd for (C11H6BrClN2O) [M+H]+, 296.9. found 296.9.

1. customthe ice bath was removed
2. additionThe reaction mixture was poured into water (2 L)
3. filtrationthe precipitate was filtered
4. washwashed with water
5. temperatureheated to 65° C. for 1 h
6. filtrationfiltered through a fritted glass
7. additionThe filtrate was treated with activated charcoal
8. temperatureheated to 65° C. for 1 h
9. filtrationfiltered through a pad of Celite
10. washwashed with hot MeOH (2 L)
11. concentrationconcentrated until the volume
12. temperatureThe residue was cooled to 0° C.
13. filtrationthe precipitate was filtered
14. washwashed with MTBE
15. customdried