Ethyl chloroformate → ethyl 2-(5-(4-fluorophenoxy)-2-(pyridin-2-yl)-1H-benzo[d]imidazol-6-yl)pyrrolidine-1-carboxylate

HRID 13283

Reaktionsgleichung

Reaktionsgleichung von HRID 13283
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[F:7][C:8]1[CH:34]=[CH:33][C:11]([O:12][C:13]2[C:27]([CH:28]3[CH2:32][CH2:31][CH2:30][NH:29]3)=[CH:26][C:16]3[NH:17][C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)=[N:19][C:15]=3[CH:14]=2)=[CH:10][CH:9]=1>[Zn].C1C=CC=CC=1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]2[C:27]([CH:28]3[CH2:32][CH2:31][CH2:30][N:29]3[C:2]([O:4][CH2:5][CH3:6])=[O:3])=[CH:26][C:16]3[NH:17][C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)=[N:19][C:15]=3[CH:14]=2)=[CH:33][CH:34]=1

Komponenten

5

Edukt 2

HCID 10928Ethyl chloroformateHCID 231455755-(4-fluoro-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

Produkt 1

HCID 23145223ethyl 2-(5-(4-fluorophenoxy)-2-(pyridin-2-yl)-1H-benzo[d]imidazol-6-yl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

5.2 mg of zinc powder and 0.006 ml of ethyl chloroformate were added in order to a benzene (1 ml) solution of 20 mg of 5-(4-fluoro-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole obtained in Example 168, and the reaction liquid was stirred overnight at room temperature. The reaction solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a white solid.

Aufarbeitung

  1. customthe reaction liquid
  2. customThe reaction solvent was evaporated away under reduced pressure
  3. customthe resulting residue was purified
  4. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-3e5e65171b8849119f3790876982c93e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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