Pyridine → 2-(3,5-Dimethyl-1H-pyrazol-1-yl)benzaldehyde

HRID 1966698Notes

Reaction equation

HRID 1966698 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O)=[O:2].[CH3:12][C:13]1[CH:17]=[C:16]([CH3:18])[NH:15][N:14]=1.N1C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:12][C:13]1[CH:17]=[C:16]([CH3:18])[N:15]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:1]=[O:2])[N:14]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 62103,5-DimethylpyrazoleHCID 2921892-Formylphenylboronic acid

Product 1

HCID 127467312-(3,5-Dimethyl-1H-pyrazol-1-yl)benzaldehydeYield 15%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-formylphenylboronic acid (500 mg, 3.33 mmol) in CH2Cl2 (30 mL) are added 3,5-dimethyl-1H-pyrazole (160 mg, 1.67 mmol), Cu(OAc)2 (909 mg, 5.0 mmol), pyridine (528 mg, 6.67 mmol) and molecular sieves (1.0 g) at room temperature. The mixture is stirred at the same temperature for 4 days with loose cap. The mixture is filtered through a short pad of diatomaceous earth and the solids are washed with CH2Cl2. The combined filtrates are concentrated and purified via flash chromatography (12 g silica gel, CH2Cl2 then 20% EtOAc/heptane) to afford 2-(3,5-dimethyl-pyrazol-1-yl)-benzaldehyde (50 mg, 8%).

Workup

  1. filtrationThe mixture is filtered through a short pad of diatomaceous earth
  2. washthe solids are washed with CH2Cl2
  3. concentrationThe combined filtrates are concentrated
  4. custompurified via flash chromatography (12 g silica gel, CH2Cl2

Sources & evidence

ORD record
ord-e4c7f03242f248b5a00807bf7257d1cb
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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