Sodium hydride → [6-Chloro-5-(2-chloro-benzoyl)-pyrazin-2-yl]-(2-fluoro-phenyl)-acetic acid methyl ester

HRID 230164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230164
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([C:12]1[C:17]([Cl:18])=[N:16][C:15](Cl)=[CH:14][N:13]=1)=[O:11].[CH3:20][O:21][C:22](=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30]>CN(C=O)C>[CH3:20][O:21][C:22](=[O:31])[CH:23]([C:15]1[CH:14]=[N:13][C:12]([C:10](=[O:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[Cl:3])=[C:17]([Cl:18])[N:16]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2733230Methyl 2-fluorophenylacetateHCID 59812791(2-Chlorophenyl)-(3,5-dichloropyrazin-2-yl)methanone

Produkt 1

HCID 59834346[6-Chloro-5-(2-chloro-benzoyl)-pyrazin-2-yl]-(2-fluoro-phenyl)-acetic acid methyl esterAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of sodium hydride (0.175 g, 7 mmol) and (2-Chloro-phenyl)-(3,5-dichloro-pyrazin-2-yl)-methanone (0.86 g, 2.99 mmol) in 5 mL DMF was added (2-Fluoro-phenyl)-acetic acid methyl ester (0.503 g, 2.99 mmol). The reaction mixture was stirred for one hour at room temperature, and then was quenched by addition of water and aqueous HCl. The aqueous mixture was extracted with methylene chloride, and the combined organic phases were dried over MgSO4, filtered, and evaporated under reduced pressure to give 1.19 g of crude [6-Chloro-5-(2-chloro-benzoyl)-pyrazin-2-yl]-(2-fluoro-phenyl)-acetic acid methyl ester. Mass Spec. M+H=419.

Aufarbeitung

  1. customwas quenched by addition of water and aqueous HCl
  2. extractionThe aqueous mixture was extracted with methylene chloride
  3. dry with materialthe combined organic phases were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9397369a694d406c9291a5ac6045c887
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566708B2

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