Sodium Carbonate → HCID 59631376, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 2,5-dibromo-3-nitropyridine (0.31 g, 1.11 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (0.26 g, 1.23 mmol), tetrakis(triphenylphosphine)palladium (64.7 mg, 0.056 mmol), and 2.0M sodium carbonate (3.0 mL, 6.00 mmol) in toluene (3.0 mL) and EtOH (1.0 mL) was heated to 70° C. After 19 h, the reaction was cooled to rt then diluted with water. After extraction with EtOAc, the organic layer was dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified on silica gel (0-20% EtOAc in hexanes) to afford a light yellow solid as 5-bromo-2-(3,6-dihydro-2H-pyran-4-yl)-3-nitropyridine. 1H NMR (400 MHz, CDCl3) δ ppm 8.81 (1H, d, J=2.0 Hz), 8.20 (1H, d, J=2.0 Hz), 6.09 (1H, m), 4.30 (2H, q, J=2.8 Hz), 3.94 (2H, t, J=5.4 Hz), 2.61 (2H, m).

Provenance & Evidence