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

HRID 79363Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[C:16]([O:22][CH3:23])=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[N:3]=1.[B-](F)(F)(F)[CH:25]=[CH2:26].[K+]>CC(O)C.C1COCC1>[CH3:23][O:22][C:16]1[C:15]([CH2:14][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([CH:25]=[CH2:26])=[N:3]2)=[CH:20][CH:19]=[C:18]([CH3:21])[N:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

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).

Workup

additionwere added
filtrationThe mixture was filtered through Celite
washthe filter pad was rinsed with ethyl acetate
washThe filtrate was washed with water and brine 3 times
concentrationThe organic phase was concentrated to a residue under vacuum
customThe residue was purified by silica gel chromatography
washeluting with 15-20% EtOAc/hexanes

Sources & evidence

ORD record: ord-a6890c3514524fd49755c6c5f74882e2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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