3-Nitrophenylboronic Acid → 1-(6-Methoxy-3'-nitro-biphenyl-3-ylmethyl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-(3-Bromo-4-methoxy-benzyl)-1H-indole (150 mg, 0.474 mmol), palladium bis(triphenylphosphine)dichloride (13.3 mg, 0.0190 mmol), and 3-nitrophenylboronic acid (94.9 mg, 0.569 mmol) in dioxane (10 mL) and 1 M aqueous sodium carbonate (1.1 mL) was stirred at 85° C. for 22 h. To the reaction was added ethyl acetate (30 mL). The organic suspension was washed with water (4×30 mL), brine (2×30 mL), dried over sodium sulfate, and the solvent removed under vacuum. The residue was purified by flash silica gel column chromatography (10% ethyl acetate in hexanes as the elutant) to yield 1-(6-Methoxy-3′-nitro-biphenyl-3-ylmethyl)-1H-indole P-010 (23.6 mg, 17% yield).

Provenance & Evidence