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

HRID 573319ノート

反応式

HRID 573319 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b27b4afb252f4bd6bb313a3265dbe281
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

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