1-Hydroxybenzotriazole → Ethyl 3-chloro-4-(1-methyl-3-indolylcarbonylamino)phenylacetate

Participants

Reaction Conditions

Reaction Steps

In DMF (20 ml), EDC HCl (1.44 g, 7.49 mmol) was added to 1-methyl-3-indolylcarboxylic acid (1.01 g, 5.71 mmol), ethyl 4-amino-3-chlorophenylacetate (1.22 g, 5.71 mmol), HOBt (0.86 g, 6.34 mmol), and DMAP (0.14 g, 1.15 mmol) and the resulting mixture was stirred at 70° C. for 18 hours. After cooling to room temperature, the reaction mixture was added with water, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (1:1, v/v) eluate fractions, ethyl (3-chloro-4-((1-methyl-3-indolylcarbonyl)amino)phenyl)acetate (639 mg, 30%) was obtained as a yellow solid.

Provenance & Evidence