(2-Methoxypyridin-4-yl)boronic acid → 4-[5-(2-Methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino]-N-pyridin-3-ylmethyl-benzamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-(5-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide (50 mg, 132 μmol), 2-methoxypyridin-4-boronic acid (40 mg, 260 μmol), Pd(PPh3)4 (46 mg, 40 μmol) and NaOtBu (51 mg, 530 μmol) in 1.2 mL of DMF/water (5:1, degassed) is degassed for 1 min in a sealed tube. The tube is sealed and the reaction mixture heated at 110° C. for five hours. After evaporation of the solvents, the residue is purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 97:3) affording the title compound (46 mg), which is isolated as a mixture containing 50% of product.

Provenance & Evidence