Salicylaldehyde oxime → HCID 70982256, compound

HRID 1409345Notes

Reaction equation

HRID 1409345 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1.C(=NO)C1C(=CC=CC=1)O.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:26][N:27]1[CH:31]=[C:30](I)[CH:29]=[N:28]1>CN(C=O)C>[CH3:26][N:27]1[CH:31]=[C:30]([N:1]2[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]2)[CH:29]=[N:28]1

Participants

6

Reactant 4

HCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 27347731-Methyl-4-iodo-1H-pyrazoleHCID 178498454HCID 178498454, compound

Product 1

HCID 70982256HCID 70982256, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Into a solution of methyl 1H-pyrazole-3-carboxylate (10 g, 79.3 mmol) in DMF (80 ml), cuprous oxide (0.567 g, 3.96 mmol), salicylaldoxime (1.08 g, 7.93 mmol), Cs2CO3 (64.4 g, 198.4 mmol) and 1-methyl-4-iodo pyrazole (16.5 g, 79.9 mmol) were added and the mixture was stirred at 110° C. for 48 h. The reaction mixture was quenched with saturated solution of aqueous NaHCO3 and extracted with EtOAc. The organic layer was concentrated and purified by flash-chromatography. Yield 2.9 g. 1H-NMR (400 MHz; DMSO-d6): δ 3.83 (s, 3H), 3.88 (s, 3H), 7.90 (s, 1H), 8.29 (d, 2H). LC-MS: [M+H]=207.

Workup

  1. customThe reaction mixture was quenched with saturated solution of aqueous NaHCO3
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated
  4. custompurified by flash-chromatography

Sources & evidence

ORD record
ord-1076760d699147fcb83cbcb8ca909eab
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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