Water → HCID 58442093, Verbindung

HRID 1256788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256788
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+].[C:12]([O:16][C:17](=[O:36])[N:18]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[C:21]([Cl:27])[N:20]=1)([CH3:15])([CH3:14])[CH3:13].O>CO>[C:12]([O:16][C:17](=[O:36])[N:18]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:19]1[CH:24]=[CH:23][C:22]([CH:25]([OH:26])[C:3]2[C:4]3[C:9](=[N:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[C:21]([Cl:27])[N:20]=1)([CH3:15])([CH3:13])[CH3:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14798Sodium HydroxideHCID 86628949HCID 86628949, Verbindung

Produkt 1

HCID 58442093HCID 58442093, VerbindungAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 1H-Pyrrolo[2,3-b]pyridine (1, 465 mg, 3.93 mmol) in methanol (50 mL) were added sodium hydroxide (0.630 g, 0.0157 mol) and (4-chloro-benzyl)-(6-chloro-5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (541, 1.5 g, 0.0039 mol). The reaction was stirred at room temperature overnight, then poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified with silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give the desired compound (542, 1.0 g, 51%). MS (ESI) [M+H+]+=499.1.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified with silica gel column chromatography
  6. washeluting with 20% to 100% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-926d3cd9ad1e40f09ec22db0d5c6a0b9
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461169B2

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