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

HRID 573319Notes

Reaction equation

HRID 573319 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b27b4afb252f4bd6bb313a3265dbe281
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

Loading…