Ammonium Chloride → 2-(Pyridin-4-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrile

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A dried flask was charged with 2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrile (1.0 g, 5.38 mmol) in DME (20 ml). The mixture was degassed and filled with N2, then t-BuOK (30 ml, 30 mmol, 1M in THF), 4-bromopyridine hydrochloride (2.1 g, 10.7 mmol) and Pd(dppf)Cl2 (39.6 mg, 0.538 mmol) was added. The mixture was stirred at 60° C. for 3 h. After cooling to room temperature, sat.aq NH4Cl (15 ml) was added and the solution was extracted with EtOAc (3×30 ml). The combined organic layers were washed with brine and dried over Na2SO4, concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc: Petroleum ether=4:1) to give 2-(pyridin-4-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrile (360 mg, yield: 25.7%). 11-1 NMR (CDCl3 400 MHz): δ8.75 (d, J=1.6; Hz, 1H), 8.71 (d, J=6.0; Hz, 2H), 7.90 (dd, J=8.0; Hz, 2.0; Hz, 1H), 7.77 (d, J=8.4; Hz, 1H), 7.31 (d, J=6.0; Hz, 2H), 5.26 (s, 1H).

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