Triethylamine → 1-((6-methoxypyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole

HRID 79296Notes

Reaction equation

HRID 79296 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:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[N:16]=2)[N:3]=1.[CH:23]([B-](F)(F)F)=[CH2:24].[K+].C(N(CC)CC)C>CC(O)C.C1COCC1>[CH3:22][O:21][C:17]1[N:16]=[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:23]=[CH2:24])=[N:3]2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 672611043-iodo-1-((6-methoxypyridin-2-yl)methyl)-4-nitro-1H-indazole

Product 1

HCID 672600471-((6-methoxypyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazoleYield 94.3%

Reagents, catalysts & solvents 1

HCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

To 3-iodo-1-((6-methoxypyridin-2-yl)methyl)-4-nitro-1H-indazole (2.65 g, 6.46 mmol) in IPA/THF (40 mL/10 mL) was added potassium vinyltrifluoroborate (1.30 g, 9.69 mmol), triethylamine (1.31 g, 12.9 mmol) and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.264 g, 0.323 mmol). The reaction mixture was heated to reflux and stirred for 16 hours. The reaction mixture was cooled to ambient temperature and concentrated to remove solvent. The residue was dissolved with EtOAc (100 mL) and washed with saturated NH4Cl, H2O and brine. The solution was dried (Na2SO4) and concentrated to provide the desired product (1.89 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customto remove solvent
  5. dissolutionThe residue was dissolved with EtOAc (100 mL)
  6. washwashed with saturated NH4Cl, H2O and brine
  7. dry with materialThe solution was dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-50f8bd1d9677421285b40aec032841ed
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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