Sodium Carbonate → Sbb062309

Participants

Reaction Steps

2-Bromo-4-methyl-5-acetylthiazole (12.0 g, 54.5 mmol) was dissolved in a mixture of dimethoxyethane (180 ml), water (76 ml) and ethanol (52 ml). To this solution was then added 3-pyridineboronic acid (20.1 g, 163.5 mmol), tetrakis(PPh3)palladium(0) (6.3 g, 5.4 mmol), and sodium carbonate (17.3 g, 163.5 mmol), and the reaction mixture was heated to 160° C. in a microwave oven for a period of 1 hour. The reaction was allowed to cool to ambient temperature, the solvents were removed by evaporation, the residue taken up in ethyl acetate, and the mixture filtered through silica gel and celite. The ethyl acetate was washed with water, dried over magnesium sulfate, and the solvent removed by evaporation. The crude product was purified by chromatograph and the product was obtained as a fawn colored solid. 1H NMR (CDCl3): 2.6 ppm (3H, s); 2.8 ppm (3H, s); 7.4 ppm (1H, m); 8.25 ppm (1H, m); 8.7 ppm (1H, m); 9.2 ppm (1H, m).

Provenance & Evidence