Methanol → {3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-carbamic acid methyl ester

HRID 60081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 60081
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:11][O:12][C:13](=[O:25])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([CH:22]=[O:23])[C:16]=1[F:24].CO.[OH-].[K+]>O>[CH3:11][O:12][C:13](=[O:25])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([CH:22]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=3)[NH:8][CH:9]=2)[OH:23])[C:16]=1[F:24]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 58368834(2,4-Difluoro-3-formyl-phenyl)-carbamic acid methyl ester

Produkt 1

HCID 58368953{3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-carbamic acid methyl esterAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Into a reaction flask under nitrogen, 5-bromo-1H-pyrrolo[2,3-b]pyridine (4, 1.00 g, 5.08 mmol) is combined with (2,4-difluoro-3-formyl-phenyl)-carbamic acid methyl ester (3, 1.09 g, 5.08 mmol), 10 mL of methanol and potassium hydroxide (0.41 g, 7.31 mmol). The reaction is stirred at room temperature overnight, then diluted with 30 mL of water and extracted with 1×50 mL, then 2×30 mL of ethyl acetate. The organic layers are combined, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with a gradient of ethyl acetate:hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (5, 1.91 g, 91%).

Aufarbeitung

  1. extractionextracted with 1×50 mL
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material is purified by silica gel column chromatography
  6. washeluting with a gradient of ethyl acetate
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-330b30895f254e13b1624ed59cbcd54f
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440969B2

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