1,4-Dioxane → 5-Amino-4,6-dimethylpicolinonitrile

Participants

Reaction Steps

4,6-dibromo-5-amino-2-cyanopyridine (1 g) was dissolved in a mixed solvent of 1,4-dioxane (10 mL) and water (1 mL). Trimethylboroxin (1.3 g), Pd(dppf)Cl2-DCM complex (264 mg) and potassium carbonate (1.5 mg) were added to the solution, and the mixture was reacted using a microwave reactor at 140° C. for four hours. The reaction mixture was returned to mom temperature and then partitioned by adding ethyl acetate and water. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 100%) to give the title compound (390 mg).

Provenance & Evidence