1,3-dimethyl-1H-pyrrole → HCID 67355881, Verbindung

HRID 1478892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478892
CN(C)[CH:3]=[C:4]([N:9]=[CH:10]N(C)C)[C:5]([O:7][CH3:8])=[O:6].[CH3:15][N:16]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17]1>C(O)(=O)C.C(O)(C(F)(F)F)=O>[CH3:15][N:16]1[C:20]2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[N:9]=[CH:10][C:19]=2[C:18]([CH3:21])=[CH:17]1

Komponenten

5

Edukt 2

HCID 109644171,3-dimethyl-1H-pyrroleHCID 86674845HCID 86674845, Verbindung

Produkt 1

HCID 67355881HCID 67355881, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

In a 500 ml round bottom flask, methyl 3-(dimethylamino)-2-((dimethylamino)methyleneamino)acrylate (1A, 12 g, 61 mmol) was dissolved in acetic acid (45 ml) and TFA (15 ml). 1,3-Dimethyl-1H-pyrrole (5.8 g, 61 mmol) was added and the mixture was stirred at room temperature for an hour and then at 110° C. for 4 hours. Volatiles were then evaporated from the reaction mixture, the residue was cooled in an ice bath and ice cold saturated K2CO3 solution (200 ml) was slowly added to it. The mixture was extracted with EtOAc (3×250 ml). Combined organic layers were then washed with brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified on a silica column using hexane-EtOAc (0-100%). Desired product methyl 1,3-dimethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (1J, 6.8 g, 55%) was obtained.

Aufarbeitung

  1. customVolatiles were then evaporated from the reaction mixture
  2. temperaturethe residue was cooled in an ice bath
  3. additionice cold saturated K2CO3 solution (200 ml) was slowly added to it
  4. extractionThe mixture was extracted with EtOAc (3×250 ml)
  5. washCombined organic layers were then washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified on a silica column

Quellen und Nachweise

ORD-Eintrag
ord-d331f50568a647939281cd8e4687cb73
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403819B2

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