Cesium carbonate → [3-Benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine

Participants

Reaction Conditions

Reaction Steps

[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine (MW=385.26, 193 mg, 0.5 mmol) was placed into a 10 mL microwave reaction tube and placed under a nitrogen atmosphere. 3,4-(Methylenedioxy)phenylboronic acid (MW=165.94, 124 mg, 0.75 mmol), 2-(di-t-butylphosphino)biphenyl (FW 298.41, 15 mg, 0.05 mmol), tris(dibenzylideneacetone)dipalladium (FW 915.75, 13 mg, 0.025 mmol), cesium carbonate (FW 325.82, 326 mg, 1 mmol) and dry dioxane (3 mL) were added to the tube. After flushing with nitrogen, the reaction tube was sealed and heated at 110° C. for 16 h. After cooling, the reaction mixture was filtered through a short pad of silica gel, and the filtrate was concentrated. The residue was purified by silica gel column chromatography using 2% methanol in methylene chloride to give [3-benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine.

Provenance & Evidence