2-Bromopyridine → 1-(Pyridin-2-yl)-1H-pyrazole-4-carbaldehyde

HRID 2374142Notes

Reaction equation

HRID 2374142 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:8]1[CH:12]=[CH:11][C:10](C=O)=[N:9]1.[C:15](=O)([O-])[O-:16].[K+].[K+]>CN(C=O)C.O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:9]1[CH:10]=[C:11]([CH:15]=[O:16])[CH:12]=[N:8]1

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 122183831H-Pyrazole-3-carbaldehyde

Product 1

HCID 247048931-(Pyridin-2-yl)-1H-pyrazole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-bromopyridine (3.4 mmol), 3-pyrazolecarboxaldehyde (3.2 mmol), and potassium carbonate (3.4 mmol) in anhydrous DMF (6 mL) was heated to 120° C. for 24 h. The reaction was cooled to RT, diluted with water, and extracted with EtOAc (3 x). The organic layers were combined and dried (Na2SO4), filtered, and concentrated. The title compound was obtained upon purification (SGC using EtOAc:hexanes gradient eluant from 0% to 100% EtOAc).

Workup

  1. temperatureThe reaction was cooled to RT
  2. extractionextracted with EtOAc (3 x)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ddf04c95c67f4704841a0f5dbde79a7b
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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