反应详情

温度

0 °C

Stir under N2 at 0° C. a mixture of 3-(4-pyridinylamino)-1H-indole-2-carboxylic acid (0.25 g, 1 mmol), benzotriazol-1-yloxytris(pyrrlidino)-phosphonium hexafluorophosphate (0.52 g, 1 mmol), diethylisopropylamine (0.175 mL, 1 mmol) and 1-methyl-2-pyrrolidinone (4.0 mL). Add 1-piperidineethanol (0.50 mL, 3.8 mmol) in one portion and stir at ambient temperature for 18.5 h. Pour the reaction into 5% aqueous potassium carbonate and extract with ethyl acetate (2×20mL). Wash the combined extract with water (20 mL), brine (20 mL), dry over MgSO4, filter and concentrate under vacuum to a dark residue. Chromatograph over silica gel (Redisep cartridge, 30 g) and elute with a step gradient of 10% methanol/dichloromethane (150 mL) to 20% methanol/dichloromethane. Concentrate like fractions under vacuum to an oil. Dry the oil under high vacuum at ambient temperature and obtain 0.14 g of the title compound as a tan foam: MS 365(M+H), TLC (silica gel, 0.5/9.5/90 ammonium hydroxide/methanol/dichloromethane) Rf=0.25.

1. additionPour
2. extractionextract with ethyl acetate (2×20mL)
3. washWash the
4. extractioncombined extract with water (20 mL), brine (20 mL)
5. dry with materialdry over MgSO4
6. filtrationfilter
7. concentrationconcentrate under vacuum to a dark residue
8. washChromatograph over silica gel (Redisep cartridge, 30 g) and elute with a step gradient of 10% methanol/dichloromethane (150 mL) to 20% methanol/dichloromethane
9. concentrationConcentrate like fractions under vacuum to an oil
10. customDry the oil under high vacuum at ambient temperature