Potassium vinyltrifluoroborate → 1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-iodo-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (982 mg, 2.31 mmol) in 10 mL of 4:1 IPA/THF was degassed for 20 minutes with an argon balloon, to which TEA (968 μL, 6.94 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (189 mg, 0.231 mmol) and potassium trifluoro(vinyl)borate (659 mg, 6.94 mmol) were added. The reaction mixture was heated at 90° C. for 3 hours. The mixture was filtered through Celite, and the filter pad was rinsed with ethyl acetate. The filtrate was washed with water and brine 3 times. The organic phase was concentrated to a residue under vacuum. The residue was purified by silica gel chromatography eluting with 15-20% EtOAc/hexanes to give the product (395 mg).

Provenance & Evidence