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Iodoacetamide → 2-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethyl]indol-1-yl}acetamide

HRID 244411
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 244411
[F:1][C:2]([F:30])([F:29])[C:3]([C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[N:9]=[CH:8]2)[OH:4].[OH-].[K+].I[CH2:34][C:35]([NH2:37])=[O:36]>CN(C=O)C>[F:30][C:2]([F:1])([F:29])[C:3]([C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]([CH2:34][C:35]([NH2:37])=[O:36])[CH:21]=1)([OH:4])[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[N:9]=[CH:8]2
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Komponenten

5

Edukt 3

HCID 3727IodoacetamideHCID 14797Potassium HydroxideHCID 249609182,2,2-trifluoro-1-(1H-indol-3-yl)-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethanol

Produkt 1

HCID 249609192-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethyl]indol-1-yl}acetamideAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a chilled (0° C.) solution of 45 mg (0.11 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-yl)-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethanol in 5 mL of DMF was added 13 mg (0.17 mmol) of powder KOH followed by 31 mg (0.17 mmol) of iodoacetamide. The mixture was stirred over night at room temperature, poured onto ice water and extracted with three 20 mL portions of ethyl acetate. The combined organic layers were dried over sodium sulfate, adsorbed on to silica gel and purified by Combiflash chromatography using EtOAc/hexanes (0-80% gradient, product eluted at 40% EtOAc) to provide a colorless film. The material from the column was crystallized from EtOAc-hexanes to afford 20 mg (39%) of the title compound as a colorless powder.

Aufarbeitung

  1. additionpoured onto ice water
  2. extractionextracted with three 20 mL portions of ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. custompurified by Combiflash chromatography
  5. customto provide a colorless film
  6. customThe material from the column was crystallized from EtOAc-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-fe24cff42f9041a6be5df12104d66299
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658637B2

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