Potassium vinyltrifluoroborate → 1-((5-fluoropyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole

HRID 79477Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([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:6][CH:7]=1.[B-](F)(F)(F)[CH:23]=[CH2:24].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CC(O)C.C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([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:23]=[CH2:24])=[N:10]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 1-((5-fluoropyridin-2-yl)methyl)-3-iodo-4-nitro-1H-indazole (0.968 g, 2.43 mmol) in 4:1 IPA/THF (10 mL) was degassed under argon. To the suspension was added TEA (0.678 mL, 4.86 mmol), potassium trifluoro(vinyl)borate (0.651 g, 4.86 mmol) and PdCl2(dppf)*dcm (0.199 g, 0.243 mmol). The mixture was then heated with stirring at 90° C. for 16 hours under argon. The mixture was allowed to cool, filtered through GF/F paper and concentrated under reduced pressure. The residue was dissolved in DCM and purified by chromatography on silica using a Biotage system, eluting with 1-10% Et2O in DCM. This gave 1-((5-fluoropyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole (229 mg).

Workup

customwas degassed under argon
temperatureThe mixture was then heated
temperatureto cool
filtrationfiltered through GF/F paper
concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in DCM
custompurified by chromatography on silica using a Biotage system
washeluting with 1-10% Et2O in DCM

Sources & evidence

ORD record: ord-db8c01992de046a6bc3560eaf1848133
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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