Dicyclohexylcarbodiimide → 1-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-(4-fluorophenyl)-2-methoxyethanone

HRID 56576Notes

Reaction equation

HRID 56576 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:12][CH3:13])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([C:39]2[CH:43]=[CH:42][NH:41][N:40]=2)[CH:34]=[CH:35][C:36]=1[O:37][CH3:38]>C1COCC1.CCOC(C)=O>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([C:39]2[CH:43]=[CH:42][N:41]([C:9](=[O:11])[CH:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[O:12][CH3:13])[N:40]=2)[CH:34]=[CH:35][C:36]=1[O:37][CH3:38]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 200621062-(4-Fluorophenyl)-2-methoxyacetic acidHCID 178488676HCID 178488676, compound

Product 1

HCID 584321411-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-(4-fluorophenyl)-2-methoxyethanoneYield 53.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-2-methoxyacetic acid (0.11 g, 0.61 mmol) in anhydrous THF (2 mL) at room temperature was added DCC (0.14 g, 0.67 mmol) in one portion. After stirring for 10 min, 3-(3,4-dimethoxyphenyl)-1H-pyrazole (0.14 g, 0.67 mmol) was added in one portion. After 48 hrs, the reaction mixture was diluted with EtOAc and the solids removed via filtration. The filtrate was concentrated in vacuo. Purification by chromatography (0-30% EtOAc-hexanes) gave the product as an oil (0.12 g, 46% yield). MS: m/z 371.1 [M+H]+.

Workup

  1. waitAfter 48 hrs
  2. customthe solids removed via filtration
  3. concentrationThe filtrate was concentrated in vacuo
  4. customPurification by chromatography (0-30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-351611fc979742aaa14828ff7e4000aa
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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