4-Methylpyrazole → 5-ethoxy-4-methyl-2-(4-methyl-1H-pyrazol-1-yl)benzaldehyde

HRID 402768Notes

Reaction equation

HRID 402768 reaction equation
Br[C:2]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11][CH2:12][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][C:15]1[CH:16]=[N:17][NH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cu]I>[CH2:12]([O:11][C:7]1[C:8]([CH3:10])=[CH:9][C:2]([N:17]2[CH:16]=[C:15]([CH3:14])[CH:19]=[N:18]2)=[C:3]([CH:6]=1)[CH:4]=[O:5])[CH3:13]

Participants

6

Reactant 3

HCID 34064-MethylpyrazoleHCID 11430Potassium CarbonateHCID 772308832-Bromo-5-ethoxy-4-methylbenzaldehyde

Product 1

HCID 866852665-ethoxy-4-methyl-2-(4-methyl-1H-pyrazol-1-yl)benzaldehydeYield 20%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-5-ethoxy-4-methylbenzaldehyde (100 mg, 0.41 mmol), 4-methyl-1H-pyrazole (40.5 mg, 0.49 mmol), K2CO3 (114 mg, 0.82 mmol), CuI (78 mg, 0.41 mmol) in DMF (2 mL) was stirred at 110° C. for 3 hours. The reaction mixture then was filtered concentrated and the residue was purified on a silica gel column eluting with 30% EtOAc in hexanes and then with 5% MeOH in DCM to provide the title intermediate (20 mg).

Workup

  1. filtrationThe reaction mixture then was filtered
  2. concentrationconcentrated
  3. customthe residue was purified on a silica gel column
  4. washeluting with 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-5a9c8b2b6ee74d57a182322d1acf3e55
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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