反应详情

温度

70 °C

To a mixture of sodium hydride (645 mg, 16.13 mmole) in DMF (10 mL) was added dropwise a solution of 7-chloro-3-(4-pyridinyl)aminobenzo[b]thiophene (3.5 g, 13.44 mmole) in DMF (35 mL) and then 4'-fluoro-4-chlorobutyrophenone ethylene ketal (3.95 g, 16.13 mmole) was added. This mixture was heated with stirring at 70° C. for three hours, poured into ice and extracted with ethyl acetate. The organics were washed twice with water, dried (MgSO4), and then concentrated. The residue was flash chromatographed (silica gel; EtOAc, then 5% MeOH/EtOAc) to obtain a dark oil, which was dissolved in methanol and treated with "Norite" to obtain 2.88 g of a white froth after concentration. Concentrated HCl (30 mL) was added and the mixture was heated on a steam bath for 45 minutes. The reaction mixture was cooled, made basic with 10% sodium hydroxide and extracted with diethyl ether. The organics were washed with water and brine, dried (MgSO4), and concentrated to obtain a froth. The froth was dissolved in methanol and ethereal hydrogen chloride, concentrated, and the frothy oil was triturated with diethyl ether. The organics were decanted and the resulting solid was recrystallized from methanol and diethyl ether to obtain 2.09 g of a white solid, mp 229° C. (dec.), after drying under high vacuum, P2O5, and refluxing xylenes.

1. temperatureThis mixture was heated
2. additionpoured into ice
3. extractionextracted with ethyl acetate
4. washThe organics were washed twice with water
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customchromatographed (silica gel
8. customEtOAc, then 5% MeOH/EtOAc) to obtain a dark oil, which
9. additiontreated with "Norite"
10. customto obtain 2.88 g of a white froth
11. concentrationafter concentration
12. additionConcentrated HCl (30 mL) was added
13. temperaturethe mixture was heated on a steam bath for 45 minutes
14. temperatureThe reaction mixture was cooled
15. extractionextracted with diethyl ether
16. washThe organics were washed with water and brine
17. dry with materialdried (MgSO4)
18. concentrationconcentrated
19. customto obtain a froth
20. concentrationethereal hydrogen chloride, concentrated
21. customthe frothy oil was triturated with diethyl ether
22. customThe organics were decanted
23. customthe resulting solid was recrystallized from methanol and diethyl ether