Sodium Carbonate → 3-(3-Quinolinyl)benzenamine

Participants

Reaction Steps

Quinoline-3-boronic acid (0.120 g, 0.693 mmol) and 3-bromoaniline (0.05 mL, 0.462 mmol) were combined in dimethoxyethane (DME, 2 mL) in a flame-dried, round-bottom flask. Sodium carbonate (Na2CO3, 2M, 0.485 mL, 0.970 mmol) and tetrakis[triphenylphosphine]palladium(0) (Pd(PPh3)4, 0.017 g, 0.014 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum, and the residue was resuspended in H20 and extracted with methylene chloride (CH2Cl2). The organic phase was dried over magnesium sulfate (MgSO4) and concentrated under vacuum. The crude product was purified by silica column chromatography (0-5% methanol (MeOH)/CH2Cl2). The purification was monitored by thin layer chromatography (TLC). The solvent was removed under vacuum from fractions containing product, resulting in 0.054 g in 53% yield.

Provenance & Evidence