2,6-Dichloro-3-pyridylamine → 6-Chloro-2-ethylpyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-amino-2,6-dichloropyridine (8.1 g, 50 mmol, purchased from TCl) in 1,4-dioxane (248 ml) was added tetrakis(triphenylphosphine)palladium(0) (920 mg, 0.80 mmol) and triethylaluminum (52 mmol, 0.94 M in hexane) at room temperature, and the mixture was stirred for 3 hours at 100° C. Themixture was quenched with 2 M HCl aqueous solution after cooling, and then it was separated between the aqueous and organic phases. The aqueous phase was extracted with EtOAc. The combined organic phases were dried over magnesium sulfate and concentrated. The crude product was purified by silica gel column chromatography, eluting with hexane/EtOAc (2:1), to give the title compound (2.73 g, 35%).

Provenance & Evidence