Ethyl Acetate → 3-Methyl-5-nitro-2-[4-(trifluoromethyl)phenyl]pyridine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-(trifluoromethyl)phenylboronic acid (285 mg, 1.5 mmol), 2-bromo-3-methyl-5-nitropyridine (216 mg, 1.0 mmol), and potassium carbonate (345 mg, 2.5 mmol) in water (1.5 mL) and dioxane (6 mL) was added tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.035 mmol). The resulting mixture was stirred at 80° C. for 4.5 hours. The mixture was cooled to room temperature. Ethyl acetate was added and the mixture was washed with water, then brine, dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave 3-methyl-5-nitro-2-(4-(trifluoromethyl)phenyl)pyridine (223 mg, 79%). 1H NMR (400 MHz, CDCl3, δ): 9.35 (s, 1 H), 8.42 (s, 1 H), 7.77 (d, 2 H), 7.69 (d, 2 H), 2.51 (s, 3 H).

Provenance & Evidence