1,1'-Carbonyldiimidazole → HCID 70102281, compound

Participants

Reaction Steps

To a solution of CDI (0.93 g, 5.7 mmol) in THF (50 mL) is added a solution of 6-bromo-5-carboxymethyl-2-methyl-1H-indole-3-carboxylic acid ethyl ester in THF (50 mL). The mixture is stirred at room temperature for 45 minutes, then refluxed for 1 hour. After cooling the reaction mixture to room temperature, 2-(3-methoxyphenyl)ethylamine is added and resulting reaction mixture is stirred at room temperature overnight. The reaction mixture is concentrated in vacuo, ethyl acetate (150 mL) is added, then washed with 1N HCl (50 mL), 1N NaOH (50 mL), and brine (50 mL). The organic layer is dried (Na2SO4) and concentrated in vacuo to give the desired product (2.15 g, 84%). MS: 473, 475 (M+1)+.

Provenance & Evidence