Triethylamine → 1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole

HRID 79372Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[C:11](I)=[N:10]2)=[N:3]1.B(O)(O)O.F[C:27]([K])=[C:28](F)F.C(N(CC)CC)C>C1COCC1.CC(O)C.CCOC(C)=O>[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[C:11]([CH:27]=[CH2:28])=[N:10]2)=[N:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-iodo-4-nitro-1H-indazole (8.35 g, 21.0 mmol) in THF/IPA (10 mL/30 mL) was added trifluorovinylpotassium borate (5.63 g, 42.0 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.858 g, 1.05 mmol) and triethylamine (8.79 mL, 63.1 mmol). The reaction mixture was heated to 80° C. for 16 hours. The mixture was diluted with EtOAc (100 mL), washed with H2O and brine, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Hexane/EtOAc 5:1) to provide the product (5.12 g).

Workup

washwashed with H2O and brine
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (Hexane/EtOAc 5:1)

Sources & evidence

ORD record: ord-2393685120a1404b9cc66a0a79ea1865
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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