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

HRID 79378Notes

Reaction equation

HRID 79378 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[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=2)[N:3]=1.B(O)(O)O.F[C:26]([K])=[C:27](F)F.C(N(CC)CC)C>C1COCC1.CC(O)C.CCOC(C)=O>[CH3:20][N:17]1[CH:18]=[CH:19][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:26]=[CH2:27])=[N:3]2)=[N:16]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67261513HCID 67261513, compoundHCID 178506051HCID 178506051, compound

Product 1

HCID 866722161-((1-methyl-1H-pyrazol-3-yl)methyl)-4-nitro-3-vinyl-1H-indazoleYield 62.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Conditions

Temperature
80 °C

Procedure

To 3-iodo-1-((1-methyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole (5.11 g, 13.3 mmol) in THF/IPA (10 mL/30 mL) was added trifluorovinylpotassium borate (3.57 g, 26.7 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.545 g, 0.667 mmol) and triethylamine (5.58 mL, 40.0 mmol). The reaction mixture was heated to 80° C. for 16 hours. The reaction mixture was diluted with EtOAc (100 mL), washed with H2O and brine. The organic phase was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexanes/EtOAc 5:1) to provide the product (2.36 g).

Workup

  1. washwashed with H2O and brine
  2. concentrationThe organic phase was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (hexanes/EtOAc 5:1)

Sources & evidence

ORD record
ord-5c9008e5ecc9438bb8b7a3cdff2d2b01
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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