Formic Acid → 6-Chloro-3H-imidazo(4,5-c)pyridine

HRID 2409048

Reaktionsgleichung

Reaktionsgleichung von HRID 2409048
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[CH:10](O)=O>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][CH:10]=[N:9][C:4]=2[CH:3]=1

Komponenten

3

Edukt 2

HCID 284Formic AcidHCID 8171336-Chloropyridine-3,4-diamine

Produkt 1

HCID 218138956-Chloro-3H-imidazo(4,5-c)pyridineAusbeute 82 %

Versuchsvorschrift

A mixture of 6-chloropyridine-3,4-diamine (4.00 g, 27.86 mmol) in formic acid (20.0 mL) was heated at reflux overnight. The reaction mixture was concentrated under reduced pressure to give a brown oil, which was partitioned between EtOAc (300 mL) and a sat'd aq NaHCO3 (100 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with a MeOH/DCM gradient (6% to 9% MeOH) to afford 3.5 g (82%) of 6-chloro-3H-imidazo[4,5-c]pyridine as white solid, MS (ESI): m/z=154.1 [M+1]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto give a brown oil, which
  5. customwas partitioned between EtOAc (300 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by SiO2 chromatography
  10. washeluting with a MeOH/DCM gradient (6% to 9% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-c8de8487b2a147cbb340f8525bd6e3f2
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815877B2

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