Potassium Carbonate → 2-(4-Chloro-pyrazol-1-yl)-5-methoxy-benzaldehyde

HRID 1966708Notes

Reaction equation

HRID 1966708 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:12][C:13]1[CH:14]=[N:15][NH:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O>[Cl:12][C:13]1[CH:14]=[N:15][N:16]([C:2]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=2[CH:4]=[O:5])[CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 275241H-Pyrazole, 4-chloro-HCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 585420082-(4-Chloro-pyrazol-1-yl)-5-methoxy-benzaldehyde

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-fluoro-5-methoxybenzaldehyde (450 mg, 2.92 mmol) in DMSO (13 mL) are added 4-chloro-1H-pyrazole (450 mg, 4.39 mmol) and K2CO3 (810 mg, 5.84 mmol) at room temperature. The solution is heated to 100° C. for 1.5 hours. The solution is cooled down and is diluted with H2O (150 mL) and extracted with EtOAc (3×). The combined organic layers are dried with MgSO4 and filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 5-25% EtOAc in heptane as the eluent to afford 2-(4-chloro-pyrazol-1-yl)-5-methoxy-benzaldehyde which is used without further purification

Workup

  1. temperatureThe solution is cooled down
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layers are dried with MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated
  6. customthe residue is purified by silica gel flash column chromatography with 5-25% EtOAc in heptane as the eluent

Sources & evidence

ORD record
ord-48f4c6f91da7487c839d132251427491
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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