Tripropylamine → 1H-Indole-5-acetic acid, 3-(ethoxycarbonyl)-2-methyl-, ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(4-ethoxycarbonylmethyl-2-iodo-phenylamino)but-2-enoic acid ethyl ester (12.5 g, 30 mmol) in DMF (30 mL), tripropylamine (4.3 g, 30 mmol), and Pd(II)acetate (0.33 g, 1.5 mmol) are added, and the reaction mixture is heated at 120° C. for 1 hour. After cooling to room temperature, ethyl acetate (150 mL) is added. The organic layer is washed with water (2×100 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude material is recrystallized from hexane/ethyl acetate to give a yellow-orange solid (3.3 g, 38%). MS: 290 (M+1)+.

Provenance & Evidence