Sodium Iodide → 8-(2,6-Dimethylbenzyloxy)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridine

HRID 1386057

Reaktionsgleichung

Reaktionsgleichung von HRID 1386057
[OH:1][C:2]1[C:3]2[N:4]([C:8]([CH2:12][OH:13])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[CH3:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:24]=1[CH2:25]Cl>CC(C)=O>[CH3:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:24]=1[CH2:25][O:1][C:2]1[C:3]2[N:4]([C:8]([CH2:12][OH:13])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 10340Sodium Carbonate2×HCID 2211542,6-Dimethylbenzyl ChlorideHCID 217173308-Hydroxy-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridine

Produkt 1

HCID 217173228-(2,6-Dimethylbenzyloxy)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridineAusbeute 27,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 8-hydroxy-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridine (0.89 g, 5.0 mmol), sodium carbonate (1.5 g), sodium iodide (0.4 g), 2,6-dimethylbenzylchloride (0.7 g, 4.5 mmol) and acetone (60 ml) was stirred overnight. More sodium carbonate (1.0 g) was added. The reaction mixture was refluxed for 2 h. The reaction mixture was filtered and the solvent was removed in vacuo. The residue was suspended in CH2Cl2/MeOH (100:5) and filtered. Vacuum evaporation of solvent gave a residue which was purified by flash chromatography eluting with CH2Cl2—MeOH (100:4), collecting fractions, and recrystallized from CH2Cl2/CH3CN to give 0.37 g of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed in vacuo
  4. filtrationfiltered
  5. customVacuum evaporation of solvent
  6. customgave a residue which
  7. customwas purified by flash chromatography
  8. washeluting with CH2Cl2—MeOH (100:4)
  9. customcollecting fractions
  10. customrecrystallized from CH2Cl2/CH3CN

Quellen und Nachweise

ORD-Eintrag
ord-4821959f6c9b4ef683677a96279dc94e
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265415B1

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