3-Bromoquinoline → 3-{3-[1-(3-Nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}quinoline

Participants

Reaction Steps

A well homogenised mixture of the Compound 1c (50 mg, 0.21 mmol), 3-bromoquinoline (0.039 ml, 0.21 mmol), bis-(triphenylphosphine)palladium dichloride (5 mg, 0.007 mmol) and tetra-butylammonium fluoride (215 mg, 0.82 mmol) was stirred at 80° C. for 1 h in a sealed vessel. The reaction mixture was cooled, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether gradient from 2:8 to 4:6) affording the title product (0.51 g).

Provenance & Evidence