Tetrahydrofuran → (2-[4-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl]ethanol

HRID 573319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573319
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[CH:39]=[CH:38][C:21]([O:22][C:23]3[N:27](CC(OCC)=O)[C:26]4[CH:34]=[CH:35][CH:36]=[CH:37][C:25]=4[N:24]=3)=[CH:20][CH:19]=2)=[N:10]1)[CH3:8].[O-]S([O-])(=O)=O.[Na+].[Na+].C1C[O:50][CH2:49][CH2:48]1>>[CH2:7]([N:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[CH:19]=[CH:20][C:21]([O:22][C:23]3[N:27]([CH:49]([OH:50])[CH3:48])[C:26]4[CH:34]=[CH:35][CH:36]=[CH:37][C:25]=4[N:24]=3)=[CH:38][CH:39]=2)=[N:10]1)[CH3:8]

Komponenten

5

Edukt 4

HCID 8028TetrahydrofuranHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 66727897Ethyl {2-[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl}acetate

Produkt 1

HCID 86688980(2-[4-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl]ethanol

Versuchsvorschrift

LiAlH4 (24.8 mg) was added to a solution of ethyl 2-{2-[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzo[d]imidazol-1-yl}acetate (144 mg) in THF (3.5 ml) at 0° C. After stirring for 1 h at the same temperature, Na2SO4.10H2O was added to the reaction mixture at 0° C. and stirred for 30 min. After Na2SO4 was added to this mixture, the precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane). The solid was crystallized from AcOEt/hexane to give the title compound (81 mg).

Aufarbeitung

  1. additionwas added to the reaction mixture at 0° C.
  2. customthe precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)
  5. customThe solid was crystallized from AcOEt/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b27b4afb252f4bd6bb313a3265dbe281
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029536B2

Notizen zur Reaktion

Wird geladen…