Potassium Carbonate → 4-Fluoro-3-(pyridin-3-yl)aniline

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 3-bromo-4-fluorophenylamine (7.92 g, 41.7 mmol), diethyl(3-pyridyl)borane (6.74 g, 45.9 mmol), tetrakis(triphenylphosphine)palladium(0) (0.96 g, 0.83 mmol) and potassium carbonate (17.26 g, 125 mmol) in 1,2-dimethoxyethane (30 ml) and water (15 ml) was heated at 80° C. for 20 h. After cooling to ambient temperature the reaction was partitioned between ethyl acetate (500 ml) and water (500 ml). The organics were washed with brine (400 ml), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by flash chromatography (silica gel, 0-20% EtOAc/CH2Cl2) gave 4-fluoro-3-(pyridin-3-yl)phenylamine (3.64 g, 46%) as a colourless oil that solidified on standing to afford a white solid: 1H NMR (360 MHz, CDCl3) δ 3.65 (2H, s), 6.65-6.72 (2H, m), 6.99 (1H, dd, J 9, 9 Hz), 7.33-7.37 (1H, m), 7.84-7.86 (1H, m), 8.58 (1H, d, J 4 Hz), 8.76 (1H, m).

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