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

HRID 1798644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798644
[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-71d83339eb8044e4afbbb63dc5d1c8bf
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343970B2

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