Iodoethane → HCID 66772095, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-ethyl-4-hydroxy-1H-indole-2-carboxylic acid ethyl ester (100 mg, 0.43 mmol) and NaH (13 mg, 0.52 mmol) was stirred in DMF (3 mL) for 10 min. Ethyl iodide (80 mg, 0.52 mmol) diluted in 1 mL of DMF was added and placed in a sealed tube. The reaction mixture was heated to 120° C. via microwave for a period of 15 min. The reaction mixture was taken up in 100 mL of EtOAc and washed with 100 mL of 0.1N hydrochloric acid, brine (50 mL), and dried over anhydrous sodium sulfate. The solvent was removed to produce 4-ethoxy-1-ethyl-1H-indole-2-carboxylic acid ethyl ester (112 mg, 100% yield) as brown oil. This material was diluted in 2 mL of methanol and 2 mL of 1N NaOH and placed in a sealed tube. The reaction mixture was heated to 120° C. via microwave for 15 min. The reaction mixture was diluted in 100 mL of EtOAc and washed with 50 mL of 1N HCl, 50 mL of brine, dried over anhydrous sodium sulfate. The solvent was removed to afford 4-ethoxy-1-ethyl-1H-indole-2-carboxylic acid (100 mg, 100% yield) as a white solid. LCMS for C13H15NO3 calcd. (m/e) 233, observed 234 (M+H).

Provenance & Evidence