Benzenamine, 4-(4-morpholinyl)- → 5-chloro-N-(4-morpholinophenyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine

Participants

Reaction Conditions

Reaction Steps

A suspension of 8-bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine (160 mg, 0.69 mmol), 4-morpholin-4-yl-phenylamine (135 mg, 0.76 mmol), sodium-tert-butoxide (93 mg, 0.96 mmol), tris(dibenzylideneacetone)dipalladium (0) (13 mg, 13.76 μmol) and Xantphos (16 mg, 27.52 μmol) in dry toluene is heated at 90° C. in a sealed tube under a nitrogen atmosphere for 16 hours. The reaction mixture is evaporated to dryness and the residue partitioned between dichloromethane and 10% aqueous citric acid. The organic phase is further washed with water (1×) and brine (1×), dried over magnesium sulfate, filtered and evaporated. The solid residue (207 mg) is purified by flash chromatography (silica gel, dichloromethane/methanol 97:3) affording the title compound (70 mg) as a solid.

Provenance & Evidence