Potassium Carbonate → 4-iodo-1-[(4-methoxyphenyl)methyl]-1H-pyrazole

HRID 38235

Reaction equation

HRID 38235 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Cl[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 770224-Iodopyrazole

Product 1

HCID 574219364-iodo-1-[(4-methoxyphenyl)methyl]-1H-pyrazoleYield 88.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

According to Scheme 6 Step 1: A suspension of 4-iodo-1H-pyrazole (26.3 mmol, 5.11 g), 1-(chloromethyl)-4-methoxybenzene (29.0 mmol, 3.95 mL) and K2CO3 (39.5 mmol, 5.46 g) in acetonitrile (150 mL) was heated at 60° C. overnight. The reaction mixture was cooled to room temperature and was filtered. The filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using DCM as eluent to afford 4-iodo-1-(4-methoxybenzyl)-1H-pyrazole (23.2 mmol, 7.3 g, 88%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-aefa367428334f35889df964d4cf7e2b
Source dataset
uspto-grants-2013_09
Patent number
US08524718B2

Linked notes

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