Bromobenzene → 2-Methyl-6-[3-(1-phenylpiperidin-4-ylidene)prop-1-ynyl]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of the compound of Example 3 (0.22 g, 1.04 mmol), bromobenzene (0.17 g, 1.04 mmol), cesium carbonate (0.68 g, 2.1 mmol), BINAP (0.031 g, 0.05 mmol), palladium(II)acetate (0.01 mg, 0.05 mmol), in anhydrous and degassed toluene (10 mL) was heated at 110° C. under a nitrogen atmosphere for 12 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 2:8) affording the title product (0.30 g).

Provenance & Evidence