2,6-Di-tert-butyl-4-methylphenol → 7-Chloro-5-(4-chlorophenyl)-2-methyl-6-vinylquinoline

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)4 (52 mg, 0.045 mmol) and PdCl2(PPh3)2 (32 mg, 0.045 mmol) were added to a mixture 7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl trifluoromethanesulfonate (1F) (194 mg, 0.45 mmol), tributyl(vinyl)stannane (0.17 mL, 0.58 mmol), lithium chloride (57 mg, 1.4 mmol) and 2,6-di-tert-butyl-4-methylphenol (cat. amount) in 1,4-dioxane (8 mL). The reaction mixture was flushed with nitrogen, heated at 80° C. for 16 hours, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with a NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product 1G (50 mg, 35%). LCMS-ESI+ (m/z): 314.2, 316.2 (M+H)+.

Provenance & Evidence