Potassium Carbonate → 3-Bromo-1-[(1-ethyl-1H-pyrazol-3-yl)methyl]-4-nitro-1H-indazole

HRID 79386

Reaction equation

HRID 79386 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.Cl.Cl[CH2:16][C:17]1[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][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]([CH2:16][C:17]2[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67261340HCID 67261340, compoundHCID 178526560HCID 178526560, compound

Product 1

HCID 672611563-Bromo-1-[(1-ethyl-1H-pyrazol-3-yl)methyl]-4-nitro-1H-indazoleYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-bromo-4-nitro-1H-indazole (Preparation B; 8.51 g, 35.2 mmol) in DMF (60 mL) was added 3-(chloromethyl)-1-ethyl-1H-pyrazole hydrochloride (6.37 g, 35.2 mmol) and K2CO3 (14.6 g, 106 mmol). The reaction mixture was stirred for 16 hours. Most of DMF was removed under reduced pressure. The remaining residue was diluted with EtOAc (300 mL) and washed with H2O. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/hexanes 1:5) to provide the product (9.26 g).

Workup

  1. customMost of DMF was removed under reduced pressure
  2. additionThe remaining residue was diluted with EtOAc (300 mL)
  3. washwashed with H2O
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (EtOAc/hexanes 1:5)

Sources & evidence

ORD record
ord-246425ffe982440fb14903c05f394427
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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