Ethyl Acetate → 6-(4-methoxyphenyl)-1H-indole

Participants

Reaction Steps

6-Bromo-1H-indole (1.00 g, 5.10 mmol) and potassium carbonate (1.41 g, 10.2 mmol) were dissolved in a mixture solution of DMF/water (4:1, 10.0 mL), and the gas included in the mixture solution was removed using ultrasonic waves and nitrogen gas. After sequentially adding 4-methoxyphenylboronic acid (853 mg, 5.61 mmol) and Pd(dppf)Cl2 (416 mg, 0.51 mmol), the mixture was stirred at room temperature in a sealed state. 2 hours later, ethyl acetate and water were added and the reaction solution was filtered using a diatomite pad. After separation of the organic layer, the aqueous layer was extracted with ethyl acetate. The collected organic layer was concentrated by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (silica gel, EA:Hx=1:4). The target compound was obtained as white solid.

Provenance & Evidence