Potassium Carbonate → 4-Ethylamino-3-nitro-6-(3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile

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Reaction Steps

Tetrakis(triphenylphosphine)palladium (2.78 g) was added under a nitrogen atmosphere to a mixture of 6-chloro-4-ethylamino-3-nitro-pyridine-2-carbonitrile (10.9 g), 4-trifluoromethyl-phenylboronic acid (10.0 g) in degassed dioxane (500 mL) and a 2M aqueous solution of potassium carbonate (60 mL). The mixture was refluxed for 4 hours then concentrated under reduced pressure. The residue was partitioned between ethyl acetate (300 mL) and water (300 mL). The aqueous layer was extracted with ethyl acetate (2×300 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed over silica gel (eluent: DCM then DCM/acetone 95/5) to afford the title compound (10.4 g, 64%). 1H NMR (DMSO-d6) δ: 8.59 (br. s, 1H); 8.50-8.40 (m, 2H); 7.91 (d, J=8 Hz, 1H); 7.79 (t, J=7 Hz, 1H); 7.74 (s, 1H); 3.65 (q, J=7 Hz, 2H); 1.24 (t, J=7 Hz, 3H). MS m/z: 337 (M+1).

Provenance & Evidence