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

HRID 512675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512675
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 584321411-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-(4-fluorophenyl)-2-methoxyethanoneAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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]+.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3822fb9619494139aa6eaf2651d70e11
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102643B2

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