反应详情

温度

0 °C

Under nitrogen, stir and cool to 0° C. a mixture of ethyl 3-(4-pyridinylamino)indole-2-carboxylate (see U.S. Pat. No. 5,328,920; 0.20 g, 0.711 mmol) in dimethylformamide (5 mL). Add a 1M solution of potassium tert-butoxide in tetrahydrofuran (0.75 mL, 0.75 mmol) in one portion, stir for 10 min, and then add ethyl bromoacetate (0.12 g, 0.72 mmol) in one portion. Stir at 0° C. for 50 min and quench the reaction into water (30 mL). Extract the aqueous mixture with ethyl acetate (2×20 mL), combine the extracts, wash with water (25 mL), brine (25 mL) and dry over MgSO4. Concentrate under vacuum, chromatograph the residue on a Redisep silica gel cartridge (10 g) eluting with 5% methanol/dichloromethane to 20% methanol/dichloromethane. Combine non-homogeneous fractions concentrate and chromatograph again as above. Combine all homogenous fractions and concentrate to obtain 0.13 g (50%) of the title compound as a white solid: MS 368(M+H).

1. stirringstir for 10 min
2. stirringStir at 0° C. for 50 min
3. customquench
4. customthe reaction into water (30 mL)
5. extractionExtract the aqueous mixture with ethyl acetate (2×20 mL)
6. washwash with water (25 mL), brine (25 mL)
7. dry with materialdry over MgSO4
8. concentrationConcentrate under vacuum, chromatograph the residue on a Redisep silica gel cartridge (10 g)
9. washeluting with 5% methanol/dichloromethane to 20% methanol/dichloromethane
10. concentrationCombine non-homogeneous fractions concentrate
11. concentrationCombine all homogenous fractions and concentrate