Water → HCID 19434326, compound

Participants

Reaction Steps

2-Ethoxycarbonyl-5-(1H-imidazol-1-ylmethyl)-1H-indole (1.00 g) was dissolved in DMF (10 ml), and thereto was added sodium hydride (156 mg, purity 60%) under ice-cooling, followed by stirring at room temperature for 1 hour. Thereto was added 1-bromo-3-chloropropane (0.39 ml ), and the mixture was stirred for 1.5 hours. 1-Bromo-3-chloropropane (0.20 ml) was added again, and the mixture was stirred at room temperature for 16 hours. Water and ethyl acetate were added to the reaction mixture for extraction, followed by washing with saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (Daisogel 15 g, elution; CHCl3 --CHCl3 /MeOH=50/1-30/1) to give 1.26 g of an oily substance (1). IR (Neat, νcm-1) 1710, 1700, 1520, 1470 1H-NMR (CDCl3, δ ppm) 1.40 (3H, t, J=6.6 Hz, CH2CH3 ), 2.29 (2H, m, CH2CH2Cl), 3.63 (2H, t, J=6.0 Hz, CH2Cl), 4.38 (2H, quart, J=6.6 Hz, CH2CH3), 4.72 (2H, t, J=6.0 Hz, NCH2), 5.20 (2H, s, C5--CH2), 6.70-7.85 (7H, indole H, imidazole H)

Provenance & Evidence