Water → tert-butyl 2-(1-(4-iodobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)acetate

HRID 1500399Notes

Reaction equation

HRID 1500399 reaction equation
[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8]1[C:9]([CH3:14])=[N:10][NH:11][C:12]=1[CH3:13])([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8]1[C:12]([CH3:13])=[N:11][N:10]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=2)[C:9]=1[CH3:14])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 9542584-Iodobenzyl bromideHCID 66707418tert-butyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetate

Product 1

HCID 68390870tert-butyl 2-(1-(4-iodobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)acetateYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (3,5-dimethyl-1H-pyrazol-4-yl)acetic acid tert.-butyl ester (10 g) in dimethylformamid (50 ml) at room temperature is added 1-bromomethyl-4-iodobenzene (15.5 g) and potassium carbonate (8.0 g). After 15 h of stirring, water is added and the reaction mixture is extracted twice with ethyl acetate. The organic layer is washed several times with water, dried over magnesium sulfate and concentrated in vacuo. The residue is purified by flash chromatography (4:1 to 3:2 cyclohexane:ethyl acetate) to yield 1-(4-iodobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl-acetic acid tert.-butyl ester (12.2 g). [M+H]=427; HPLC retention time 1.57 min (Method E).

Workup

  1. extractionthe reaction mixture is extracted twice with ethyl acetate
  2. washThe organic layer is washed several times with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography (4:1 to 3:2 cyclohexane:ethyl acetate)

Sources & evidence

ORD record
ord-95c78ed372164227b9144b6643cc8019
Source dataset
uspto-grants-2015_12
Patent number
US09206164B2

Reaction notes

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