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

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Reaction Conditions

Reaction Steps

A stirred mixture 4-amino-6-chloro-3-nitro-pyridine-2-carbonitrile (152 mg, 0.76 mmol), 4-methoxy-3-trifluoromethylphenylboronic acid (332 mg,1.51 mmol), tetrakis(triphenylphosphine)palladium(0) (115 mg, 10 mol %), potassium carbonate (418 mg, 3.03 mmol) and THF (5 ml) was degassed under a stream of nitrogen before heating in the Smith Creator microwave at 150° C. for 10 minutes. The crude mixture was concentrated under reduced pressure to remove THF before partitioning between ethyl acetate (20 ml) and water (20 ml). The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure to give a dark brown oil. Mixture was flash chromatographed over silica (10 g Combiflash cartridge, 7:3 heptane/ethyl acetate to 1:1 heptane/ethyl acetate) to afford 68 mg of 4-amino-6-(4-methoxy-3-trifluoromethyl-phenyl)-3-nitro-pyridine-2-carbonitrile as an orange solid. 1H NMR (DMSO) δ 8.25 (d, 1H), 8.18 (m, 2H), 7.62 (s, 2H), 7.46 (d, 1H), 3.99 (s, 3H). MS m/z 339.3 (M+1).

Provenance & Evidence