Salicylaldehyde oxime → (1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-4-yl)methanol

HRID 1027171Notes

Reaction equation

HRID 1027171 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][NH:6][CH:7]=1.C(=NO)C1C(=CC=CC=1)O.C(=O)([O-])[O-].[Cs+].[Cs+].I[C:25]1[C:26]([Br:33])=[C:27]([O:31][CH3:32])[CH:28]=[CH:29][CH:30]=1>CN(C)C=O>[Br:33][C:26]1[CH:25]=[CH:30][C:29]([N:5]2[CH:4]=[C:3]([CH2:2][OH:1])[CH:7]=[N:6]2)=[CH:28][C:27]=1[O:31][CH3:32]

Participants

6

Reactant 4

HCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 30152104-HydroxymethylpyrazoleHCID 236362102-Bromo-3-iodoanisole

Product 1

HCID 86710564(1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-4-yl)methanolYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(hydroxymethyl)pyrazole (500 mg, 5.10 mmol), salicylaldoxime (140 mg, 1.019 mmol), cesium carbonate (4.98 g, 15.29 mmol), cuprous oxide (58.2 mg, 0.306 mmol), iodobromoanisole (1.59 g, 5.10 mmol) and N,N-dimethyl-formamide (10 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 reaction mixture was cooled to RT, then filtered through celite, and the filtrate was concentrated in vacuo. The crude material was purified by column chromotography (10% to 60% EtOAc in heptanes) to give (1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-4-yl)methanol (800 mg, MS: 285.3 [M+H+].)

Workup

  1. customvial fitted with an N2 inlet and magnetic stir bar
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe crude material was purified by column chromotography (10% to 60% EtOAc in heptanes)

Sources & evidence

ORD record
ord-2e83621e5fee4a4e85f60d0c7bd8d5e1
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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