Tributylvinyltin → 5-Bromo-2,7-dimethyl-6-vinylquinoline

Participants

Reaction Conditions

Reaction Steps

PdCl2(PPh3)2 (207 mg, 0.30 mmol) was added to a solution of 5-bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate (1.13 g, 2.95 mmol), tributyl-vinyl-stannane (0.95 mL, 3.25 mmol), and lithium chloride (375 mg, 8.85 mmol) in DMF (30 mL). The reaction mixture was flushed with nitrogen, and heated at 80° C. for 4 hours. The mixture was diluted with ethyl acetate, washed with NaHCO3 solution, water and brine, and dried over Na2SO4. Concentration and purification by flash column chromatography yielded 5-bromo-2,7-dimethyl-6-vinylquinoline. LCMS-ESI+ (m/z): [M+H]+ calc'd for C13H13BrN: 262.0; Found: 262.1.

Provenance & Evidence