3-Nitrophenylboronic Acid → HCID 66955149, compound

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 DMF/water (4:1, 10 mL) mixture solution, and then the gas included in the mixture solution was removed using ultrasonic wave and nitrogen gas. After sequentially adding 3-nitrophenylboronic 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 reactor. 2 hours later, after adding ethyl acetate and water, the reaction solution was filtered through a diatomite pad. The organic layer was separated from the filtrate and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried with anhydrous magnesium sulfate and then concentrated. Purification of the residue by chromatography (silica gel, EA:Hx=1:4) yielded the target compound as white solid.

Provenance & Evidence