3-(Methylsulfanyl)prop-1-yne → HCID 178503675, compound

Participants

Reaction Steps

A mixture of N-[(4-Chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-iodo-3-quinolinecarboxamide from Example No. 5 (1.57 g), propargyl methyl sulfide (0.355 g, 4.12 mmol), copper iodide (0.125 g), and dichlorobis(triphenylphosphine)palladium (II) (0.462 g) in diethylamine (38 mL) are stirred at room temperature overnight. An additional 0.092 g of propargyl methyl sulfide is added, and the mixture is stirred another 5 h. The reaction mixture was then concentrated in vacuo, and the residue is suspended in water (100 mL) and extracted with three portions of EtOAc. The combined organic layers are then dried over MgSO4, filtered, and concentrated in vacuo. Column chromatography (elution with 5-10%MeOH/CH2Cl2) yielded the title compound as a solid.

Provenance & Evidence