反应详情

A mixture of 3-[3-iodopropyl]-5-nitro-1H-indole (1.4 g, 4.2 mmol), 1-(3-methoxy-4-pyridinyl)-piperazine (0.98 g, 5.09 mmol) and K2CO3 (1.4 g, 10.2 mmol) in 30 mL of acetonitrile was heated to reflux for 4 h. The reaction mixture was cooled and stirred for 12 h. The solvent was removed and the residue dissolved in ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate. The organic extracts were dried (MgSO4) and concentrated, and the gummy residue was purified by flash silica gel chromatography (5% methanol in dichloromethane as eluant) to give 3-[3-[4-(3-methoxy-4-pyridinyl)-1-piperazinyl]propyl]-5-nitro-1H-indole, (0.6 g, 36%) as a yellow solid: IR (KBr) 3600, 2400, 1600, 1520, 1330, 1250, 815 cm-1 ; 1H NMR (DMSO-d6, 300 MHz) δ8.52 (d, J=2.2 Hz, 1H), 8.10 (s, 1H), 8.02 (d, J=5.3 Hz, 1H), 7.96 (dd, J=2.3, 9.0 Hz, 1H), 7.48. (d, J=9.0 Hz, 1H), 7.42 (s, 1H), 6.81 (d, J=5.4 Hz, 1H), 3.84 (s, 3H), 3.21 (br s, 4H), 3.07 (dd, J=6.4, 14.7 Hz, 2H), 2.79 (t, J=14.7 Hz, 2H), 2.66 (br s, 4H), 1.97 (m, 2H); MS (m/e) 395 (M+).

1. temperaturewas heated
2. temperatureto reflux for 4 h
3. temperatureThe reaction mixture was cooled
4. customThe solvent was removed
5. dissolutionthe residue dissolved in ethyl acetate
6. customThe aqueous layer was separated
7. extractionextracted with ethyl acetate
8. dry with materialThe organic extracts were dried (MgSO4)
9. concentrationconcentrated
10. customthe gummy residue was purified by flash silica gel chromatography (5% methanol in dichloromethane as eluant)