Salicylaldehyde oxime → HCID 86710569, compound

HRID 1027176Notes

Reaction equation

HRID 1027176 reaction equation
Cl.Cl.[NH:3]1[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4]1.C(=NO)C1C(=CC=CC=1)O.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:25][C:26]1[CH:31]=[CH:30][C:29](I)=[CH:28][C:27]=1[O:33][CH3:34]>CN(C)C=O>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([N:3]2[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4]2)=[CH:28][C:27]=1[O:33][CH3:34]

Participants

6

Reactant 4

HCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 121872021-Bromo-4-iodo-2-methoxybenzeneHCID 133489691H-Pyrazol-4-amine--hydrogen chloride (1/2)

Product 1

HCID 86710569HCID 86710569, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of pyrazole-4-amine dihydrochloride (0.75 g, 4.79 mmol), salicylaldoxime (0.131 g, 0.96 mmol), cesium carbonate (4.69 g, 14.38 mmol), cuprous oxide (0.06 g, 0.29 mmol), 1-bromo-4-iodo-2-methoxybenzene (1.5 g, 4.79 mmol) and N,N-dimethyl-formamide (5 mL) were combined in a microwave vial fitted with an N2 inlet and magnetic stir bar. The reaction mixture was stirred under a nitrogen atmosphere at 90° C. overnight. The solution obtained was allowed to cool to RT, then filtered through celite and the filtrate was concentrated in vacuo. The crude material was purified by silica gel chromotography (10% to 60% EtOAc in heptanes) to give 1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-4-amine (250 mg, MS: 270.2 [M+H+].)

Workup

  1. customvial fitted with an N2 inlet and magnetic stir bar
  2. customThe solution obtained
  3. temperatureto cool to RT
  4. filtrationfiltered through celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude material was purified by silica gel chromotography (10% to 60% EtOAc in heptanes)

Sources & evidence

ORD record
ord-c9fd3502863a4db9b4f9aab4cc974de2
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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