Ethylene Glycol → HCID 118036781, Verbindung

HRID 1778038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778038
[NH:1]1[C:5]2=[N:6][C:7]([CH:10]=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH2:12](O)[CH2:13][OH:14].CCCP(=O)=O>CCOC(C)=O.C([O-])(O)=O.[Na+]>[O:11]1[CH2:12][CH2:13][O:14][CH:10]1[C:7]1[N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]2=[CH:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 174Ethylene GlycolHCID 16167369Propylphosphoric anhydrideHCID 247288931H-Pyrrolo[2,3-b]pyridine-6-carbaldehyde

Produkt 1

HCID 118036781HCID 118036781, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1H-pyrrolo[2,3-b]pyridine-6-carbaldehyde (840 mg, 5.60 mmol), ethylene glycol (3.13 ml, 56.0 mmol) and propylphosphonic anhydride (50% in EtOAc, 3.34 ml, 5.60 mmol) in EtOAc (15 ml) was stirred at 80° C. After 18 h, the reaction mixture was cooled to room temperature, diluted with sat. aq. NaHCO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The crude material was applied to a 120 g RediSep® silica column and purified by normal phase chromatography, eluting with EtOAc. Product-containing fractions were combined and evaporated. The residue was triturated with Et2O to give the title compound as an white solid. (UPLC-MS 6) tR 0.66; ESI-MS 191.1 [M+H]+.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custompurified by normal phase chromatography
  7. washeluting with EtOAc
  8. customevaporated
  9. customThe residue was triturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-3dcf9456861f402eb3a64308ea589e06
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266883B2

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