Potassium Phosphate, Tribasic → 2-Amino-6-(3-thienyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-amino-6-bromopyridine (Lancaster, 5.0 g; 28.9 mmol; 1.0 eq.), 3-thienylboronic acid (4.44 g; 34.7 mmol; 1.2 eq.), potassium phosphate (12.27 g; 57.8 mmol; 2.0 eq.) in dry dioxane (150 mL) was added 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium (1.06 g; 1.44 mmol; 0.05 eq.) under inert atmosphere. The reaction mixture was heated at 80° C. overnight, cooled down to rt, filtered on a bed of celite and filtrates were evaporated under reduced pressure. Purification of the crude by flash chromatography on silica (gradient EtOAc/c-Hex, 5:95 to 50:50) gave the title compound as a beige solid (3.71 g, 73%). HPLC, Rt: 1.51 min. (purity 96.4%). LC/MS, M+(ESI): 177.4.

Provenance & Evidence