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Triethyl orthoacetate → 5-bromo-2-methyl-3H-imidazo[4,5-b]pyridine

HRID 1368237
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1368237
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([Br:9])[N:3]=1.[C:10](OCC)(OCC)(OCC)[CH3:11]>C(O)(=O)C.ClCCl.C(=O)([O-])[O-].[K+].[K+].C>[Br:9][C:4]1[N:3]=[C:2]2[N:1]=[C:10]([CH3:11])[NH:8][C:7]2=[CH:6][CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 2

HCID 66221Triethyl orthoacetateHCID 223883866-Bromopyridine-2,3-diamine

Produkt 1

HCID 223879615-bromo-2-methyl-3H-imidazo[4,5-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 297MethaneLösungsmittelHCID 6344Dichloromethane
Lösungsmittel
HCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

2,3-Diamino-6-bromopyridine (8.16 g) and triethyl orthoacetate (12.0 ml) were mixed in acetic acid (41 ml), and the mixture was refluxed under heating for 29 hr. After allowing to cool, the solvent was evaporated under reduced pressure to give a crude product (10 g). This was dissolved in a sufficient amount of dichloromethane and anhydrous potassium carbonate and active charcoal were added. The mixture was stirred at room temperature. The insoluble matter was removed by filtration and the solvent was evaporated to give 5-bromo-2-methyl-1H-imidazo[4,5-b]pyridine (7.59 g) as a pale-yellow powder.

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 29 hr
  3. temperatureto cool
  4. customthe solvent was evaporated under reduced pressure
  5. customto give a crude product (10 g)
  6. additionwere added
  7. customThe insoluble matter was removed by filtration
  8. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6b6e3bb323c94449840e832bdb77bb93
Quelldatensatz
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06573274B1

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