Dimethylamine → [5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-acetonitrile

HRID 472054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472054
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2].[CH2:20]=O.C[NH:23][CH3:24].[C-]#N.[K+]>CCO>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[C:19]([CH2:20][C:24]#[N:23])=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 9032Potassium CyanideHCID 116732465-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Produkt 1

HCID 67152507[5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 5-(2,6-Diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (1 g, 4.5 mmol), formaldehyde (37% solution in water, 1.4 mL, 18 mmol), dimethylamine (2 M solution in MeOH, 18 mL, 18 mmol) and EtOH (50 mL) is heated to reflux for 2.5 h. All volatiles are removed under reduced pressure. The residue is mixed with toluene, which is subsequently removed under reduced pressure. The residue is dissolved in DMF (15 mL), KCN (2.6 g, 40 mmol) is added and the mixture was refluxed for 2 h. DMF is removed under reduced pressure, and the residue is purified by chromatography on silica gel (EtOAc) to afford [5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-acetonitrile as colorless oil.

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux for 2.5 h
  3. customAll volatiles are removed under reduced pressure
  4. additionThe residue is mixed with toluene, which
  5. customis subsequently removed under reduced pressure
  6. dissolutionThe residue is dissolved in DMF (15 mL)
  7. temperaturethe mixture was refluxed for 2 h
  8. customDMF is removed under reduced pressure
  9. customthe residue is purified by chromatography on silica gel (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-bb504efe10d24e83bf56a75281442422
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633193B2

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