Sodium Carbonate → HCID 59631229, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,5-dibromo-3-nitropyridine (0.533 g, 1.89 mmol), 2-methoxyphenylboronic acid (0.29 g, 1.91 mmol), trans-dichlorobis(triphenylphosphine)-palladium (II) (68.9 mg, 0.098 mmol), and 2.0M sodium carbonate (2.9 mL, 5.8 mmol) in 1,4-dioxane (6 mL) was degassed by nitrogen. The mixture was heated to 90° C. After 7 h, the reaction was cooled to rt, then treated with water. After extracting twice with EtOAc, the organic layer was combined and dried over anhydrous magnesium 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-(2-methoxyphenyl)-3-nitropyridine. 1H NMR (400 MHz, CDCl3) δ ppm 8.93 (1H, d, J=2.2 Hz), 8.37 (1H, d, J=2.0 Hz), 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.51 (1H, m), 7.16 (1H, td, J=7.5, 1.0 Hz), 6.92 (1H, dd, J=8.3, 0.9 Hz), 3.72 (3H, s).

Provenance & Evidence