反应详情

A mixture of 2-benzoyl-6-chloro-3-(chloroacetylamino)-1-(ethoxycarbonyl)indole (step 1, 890 mg, 2.12 mmol) and dimethylamine hydrochloride (520 mg, 6.36 mmol) in DMF (30 ml) was stirred for 2 h. Water (80 ml) was added and the mixture extracted with an ethyl acetate-toluene mixture (2:1 v/v, 30 ml×2). The combined organic extracts were washed consecutively with water (50 ml) and brine (50 ml), dried (MgSO4) and evaporated. The residue was treated with a solution of 1N aqueous KOH (20 ml) and EtOH (40 ml) for 1 h, volatiles removed by evaporation and the residue extracted with ethyl acetate (30 ml×2). The combined organic extracts were dried (MgSO4) and evaporated. The crude product was recrystallized from ethyl acetate/hexane to give 350 mg (47%) of the title compound as a yellow solid. m.p.: 175-176° C. 1H-NMR (CDCl3) δ: 10.60 (1H, br s), 8.83 (1H, br s), 8.08 (1H, d, J=8.8 Hz), 7.88-7.70 (2H, m), 7.68-7.42 (3H, m), 7.29 (1H, d, J=1.8 Hz), 7.07 (1H, dd, J=1.8, 8.8 Hz), 3.04 (2H, s), 2.33 (6H, s)

1. extractionthe mixture extracted with an ethyl acetate-toluene mixture (2:1 v/v, 30 ml×2)
2. washThe combined organic extracts were washed consecutively with water (50 ml) and brine (50 ml)
3. dry with materialdried (MgSO4)
4. customevaporated
5. additionThe residue was treated with a solution of 1N aqueous KOH (20 ml) and EtOH (40 ml) for 1 h
6. customvolatiles removed by evaporation
7. extractionthe residue extracted with ethyl acetate (30 ml×2)
8. dry with materialThe combined organic extracts were dried (MgSO4)
9. customevaporated
10. customThe crude product was recrystallized from ethyl acetate/hexane