Stannane, tributyl(1-ethoxyethenyl)- → 6-(1-(6-(1-Ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)ethyl)-5,7-difluoroquinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(1-(6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)ethyl)-5,7-difluoroquinoline (423.0 mg, 1.2 mmol), Pd(Ph3P)4 (125.0 mg, 0.12 mmol) and tributyl(1-ethoxyvinyl)stannane (781.0 mg, 2.2 mmol) in DMF (5 mL) was purged with nitrogen and then heated at 100° C. for 12 hours. After removal of the solvent under reduced pressure, the residue was diluted with DCM, washed sequentially with aqueous KF and water, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography on silica gel with gradient (DCM/MeOH=50:1) to give the title compound as a yellow solid (370 mg, 91%). LCMS (method E): [MH]+=383, tR=4.24 min.

Provenance & Evidence