反应详情

温度

80 °C

To a solution of 3-methyl-1H-indole-6-carboxylic acid methyl ester (2.5 g, 13.2 mmol) in DMF (25 mL), a solution of NaH (580 mg, 14.5 mmol, 60% dispension in grease) in DMF (25 mL) is slowly added under a N2 atmosphere. The mixture is stirred at 80° C. for 20 min, and cooled to RT before the addition of 1-bromo-3-methoxypropane (4.04 g, 26.4 mmol). The resulting mixture is stirred for 24 h. 1-Bromo-3-methoxypropane (2.02 g, 13.2 mmol) and NaH (580 mg, 14.5 mmol) are added and the mixture further stirred for 24 h to complete the reaction. The solvent is concentrated under reduced pressure and the mixture diluted with AcOEt. An aqueous saturated solution of NaHCO3 is added, the layers are separated, and the aqueous one is back-extracted with AcOEt. The combined organic extracts are dried over Na2SO4, filtered and concentrated. The crude residue is purified by flash chromatography on silica gel (eluent: c-hexane/AcOEt 80:20) to give the title compound. MS (LC-MS): 262.0 [M+H]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mumin): 5.80 min.

1. stirringThe resulting mixture is stirred for 24 h
2. stirringthe mixture further stirred for 24 h
3. customthe reaction
4. concentrationThe solvent is concentrated under reduced pressure
5. additionthe mixture diluted with AcOEt
6. additionAn aqueous saturated solution of NaHCO3 is added
7. customthe layers are separated
8. extractionthe aqueous one is back-extracted with AcOEt
9. dry with materialThe combined organic extracts are dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customThe crude residue is purified by flash chromatography on silica gel (eluent: c-hexane/AcOEt 80:20)