Sodium Carbonate → 5-Bromo-2-(4-methoxyphenyl)-3-nitropyridine

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 2,5-dibromo-3-nitropyridine (0.2563 g, 0.909 mmol), 4-methoxyphenylboronic acid (0.14 g, 0.93 mmol), tetrakis(triphenylphosphine)-palladium (0.072 g, 0.062 mmol), and 2.0M sodium carbonate (2.3 mL, 4.60 mmol) in toluene (3.0 mL) and ethanol (1.0 mL) was heated to 70° C. After 2.5 h, the reaction was cooled to rt then diluted with water. After extraction with EtOAc, the organic extraction was dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified on silica gel (0-15% EtOAc in hexanes) to afford a yellow solid as 5-bromo-2-(4-methoxyphenyl)-3-nitropyridine. 1H NMR (400 MHz, CDCl3) δ ppm 8.88 (1H, d, J=2.0 Hz), 8.23 (1H, d, J=2.2 Hz), 7.53 (2H, m), 6.99 (2H, m), 3.87 (3H, s).

Provenance & Evidence