Potassium Phosphate, Tribasic → 1-(2-Fluorophenyl)-1H-indazol-4-amine

HRID 418762Notes

Reaction equation

HRID 418762 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([NH2:10])[C:4]=2[CH:3]=[N:2]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC.[F:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1I>CCOC(C)=O.[Cu]I.C1(C)C=CC=CC=1>[F:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([NH2:10])[C:4]=2[CH:3]=[N:2]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 676731-Fluoro-2-iodobenzeneHCID 413085NoName_3327HCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 576159581-(2-Fluorophenyl)-1H-indazol-4-amineYield 52.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1H-Indazol-4-amine (1.83 g, 10 mmol), copper (I) iodide (95 mg. 0.5 mmol) and potassium phosphate (4.46 g, 21 mmol) were stirred together. The flask was evacuated and refilled with argon twice. To the flask was then added trans-N,N′-dimethyl-1,2-cyclohexanediamine (320 μL, 2 mmol), 2-fluoro-1-iodobenzene (2.66 g, 12 mmol) and toluene (30 mL) and the mixture was heated at 110° C. overnight. The reaction mixture was diluted with EtOAc, filtered through Celite to remove inorganics and the Celite pad was washed successively with EtOAc until the solvent ran clear. The reaction mixture was evaporated and the residue was purified by column chromatography eluting with dichloromethane then with dichloromethane:EtOAc 9:1 to give the title compound as a yellow oil (1.19 g) which solidified on standing.

Workup

  1. customThe flask was evacuated
  2. additionrefilled with argon twice
  3. filtrationfiltered through Celite
  4. customto remove inorganics
  5. washthe Celite pad was washed successively with EtOAc until the solvent
  6. customThe reaction mixture was evaporated
  7. customthe residue was purified by column chromatography
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-f308beedf48e48bd9df305e673fb24cc
Source dataset
uspto-grants-2012_01
Patent number
US08093281B2

Reaction notes

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