Reaction #195

Reaction equation

CCOC(=O)c1cc2cccc(Br

c1ccc(CCN2CCNCC2)nc1

→

CCOC(=O)c1cc2cccc(N3

Yield 19.0%

Solvents

C1COCCO1

Conditions

Procedure

The reaction mixture of ethyl 7-bromobenzofuran-2-carboxylate (2.0 g, 7.43 mmol), 1-(2-(pyridin-2-yl)ethyl)piperazine (1.564 g, 8.18 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.476 g, 0.52 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.496 g, 1.04 mmol) and Cesium carbonate (3.63 g, 11.15 mmol) in dioxane (30 mL) (degassed with argon for 10 min) was heated at 95 °C under argon for 5 h. After cooling, the reaction mixture was filtered and concentrated. The product was purified twice by isco, the first using DCM:MeOH (0-5%) and the second time using DCM:MeOH (0-3%).

Source