Sodium Chloride → 3-(6-Methoxypyridin-2-yl)thiophene-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a 500 mL flask was added 2-formylthiophene-3-boronic acid (30A, 5.00 g, 32.1 mmol, 1.0 eq.), 2-bromo-6-methoxypyridine (30B, 6.03 g, 32.1 mmol, 1.0 eq.), toluene (100 mL), EtOH (100 mL), aqueous sodium carbonate (2N, 32 ml, 64 mmol, 2.0 eq.), and Pd(dppf)Cl2 (1.17 g, 1.6 mmol, 0.05 eq.). The reaction was stirred overnight at 90° C. The reaction was cooled and saturated aqueous NaCl (100 mL) was added and the mixture was stirred for 20 min. The reaction mixture was extracted with EtOAc (2×100 mL) and the resulting organic layers were combined and passed through a Celite pad to remove residual Pd. The organic phases were washed with a succession of H2O (100 mL) and saturated aqueous NaCl (100 mL) and then dried over anhydrous Na2SO4, filtered, and concentrated to give a bubbly brown solid that was used in the next step without further purification (6.2 g, 88%). ESI-MS: m/z 220.2 (M+H)+.

Provenance & Evidence