Benzaldehyde → HCID 67287111, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromopyridin-2-amine (0.500 g, 2.89 mmol) in toluene (10 ml) was added benzaldehyde (0.313 g, 2.95 mmol), and the reaction was stirred for 30 minutes. To this, p-tolylboronic acid (0.471 g, 3.47 mmol), sodium carbonate (0.368 g, 3.47 mmol), and water (10 ml) were added, and the reaction was degassed with argon. Tetrakis(triphenylphosphine)palladium (0.167 g, 0.144 mmol) was added, and the reaction was heated to 100° C. for 60 hours. The reaction was diluted with 10 ml of toluene and 10 ml of water, and the organic layer was collected. The organic layer was treated with 4M hydrogen chloride in dioxane (1.44 ml, 5.78 mmol) dropwise with vigorous stirring. The resulting solid was collected via filtration to yield pure 6-p-tolylpyridin-2-amine hydrochloride (0.564 g, 2.56 mmol, 88.4% yield).

Provenance & Evidence