Salicylaldehyde oxime → HCID 86710576, compound

HRID 579329Notes

Reaction equation

HRID 579329 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[O:9][CH3:10].[NH2:11][C:12]1[CH:16]=[CH:15][NH:14][N:13]=1.C(=NO)C1C(=CC=CC=1)O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:14]2[CH:15]=[CH:16][C:12]([NH2:11])=[N:13]2)=[CH:4][C:3]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 121872021-Bromo-4-iodo-2-methoxybenzeneHCID 178418806HCID 178418806, compound

Product 1

HCID 86710576HCID 86710576, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 1-bromo-4-iodo-2-methoxybenzene (2.5 g, 7.99 mmol), 3-aminopyrazole (0.797 g, 9.59 mmol), salicylaldoxime (0.219 g, 1.598 mmol), Cu2O (91 mg, 0.479 mmol), and Cs2CO3 (3.9 g, 11.98 mmol) in DMF (8 mL) was degassed with N2 and heated at 95° C. overnight. After cooling to RT, the mixture was filtered through celite and rinsed with EtOAc. The filtrate was washed with water and brine. The organic solution was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (10%-60% EtOAc in Heptane) to give 1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-3-amine (800 mg, MS: 270.3 [M+H+]).

Workup

  1. customwas degassed with N2
  2. temperatureAfter cooling to RT
  3. filtrationthe mixture was filtered through celite
  4. washrinsed with EtOAc
  5. washThe filtrate was washed with water and brine
  6. dry with materialThe organic solution was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography (10%-60% EtOAc in Heptane)

Sources & evidence

ORD record
ord-65197efeb2fb4054af94fa5ae0eb04a9
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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