Potassium Carbonate → 3-(4-Methyl-2-nitro-phenyl)-pyridine

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4-Bromo-2-nitro-phenol (648 mg, 3.0 mmol) and 3-pyridyl boronic acid (387 mg, 3.15 mmol) were diluted with 5 mL of dioxane and placed under N2. Potassium carbonate was diluted in 1 mL of H2O and added to the reaction mixture. Tetrakis(triphenylphosphine) palladium (173 mg, 0.15 mmol) was added, then the reaction was heated to 70° C. and stirred overnight. The reaction was allowed to cool to room temperature, then diluted with 30 mL of EtOAc and 30 mL of 10% Na2CO3. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The material was purified with a Biotage 40M cartridge eluting with hexanes/EtOAc, 1/1 to yield an off white solid.

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