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Sodium Iodide → 2,3-Dimethyl-8-(2,6-dimethylbenzylamino)imidazo[1,2-a]pyridine

HRID 1369589
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1369589
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[CH3:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:23]=1[CH2:24]Cl>CC(C)=O>[CH3:11][C:9]1[N:10]=[C:3]2[C:2]([NH:1][CH2:24][C:23]3[C:26]([CH3:30])=[CH:27][CH:28]=[CH:29][C:22]=3[CH3:21])=[CH:7][CH:6]=[CH:5][N:4]2[C:8]=1[CH3:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 218739802,3-Dimethylimidazo[1,2-a]pyridin-8-amine

Produkt 1

HCID 226726292,3-Dimethyl-8-(2,6-dimethylbenzylamino)imidazo[1,2-a]pyridineAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel

Versuchsvorschrift

A mixture of 8-amino-2,3-dimethylimidazo[1,2-a]pyridine (0.7 g, 4.34 mmol), sodium carbonate (2.0 g), sodium iodide (0.3 g), 2,6-dimethylbenzylchloride (0.671 g, 4.34 mmol) and acetone (30 ml) was stirred overnight. The reaction mixture was filtered and the solvent was removed in vacuo. The residue was dissolved in methylene chloride and washed with aqueous NaHCO3. The organic layer was separated and the solvent was evaporated. The crude product was purified by flash chromatography eluting with CH2Cl2/MeOH to give 0.7 g of the title compound.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with aqueous NaHCO3
  5. customThe organic layer was separated
  6. customthe solvent was evaporated
  7. customThe crude product was purified by flash chromatography
  8. washeluting with CH2Cl2/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-a0a09017e3ad4039bfd5d74fa0eada0a
Quelldatensatz
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06579884B1

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