Sodium Hydroxide → 8-(4-Methoxy-2,6-dimethylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1369559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1369559
[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.[CH3:13][O:14][C:15]1[CH:22]=[C:21]([CH3:23])[C:18]([CH:19]=O)=[C:17]([CH3:24])[CH:16]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:13][O:14][C:15]1[CH:22]=[C:21]([CH3:23])[C:18]([CH2:19][NH:1][C:2]2[C:3]3[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=3)[CH:5]=[CH:6][CH:7]=2)=[C:17]([CH3:24])[CH:16]=1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 8167794-Methoxy-2,6-dimethylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 218739802,3-Dimethylimidazo[1,2-a]pyridin-8-amine

Produkt 1

HCID 98396428-(4-Methoxy-2,6-dimethylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridineAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

8-amino-2,3-dimethylimidazo[1,2-a]pyridine (0.5 g, 3.1 mmol), 4-methoxy-2.6-dimethylbenzaldehyd (0.51 g, 3.11 mmol) were dissolved in methanol (10 ml) whereupon zinc chloride (0.51 g, 3.82 mmol) dissolved in methanol (5 ml) was added. Sodium cyanoborohydride was added in portions and the mixture was refluxed for 3 h under under nitrogen. The mixture was stirred at 0-5° C. and 1 M sodium hydroxide (20 ml) was added. After extraction with 2×50 ml of methylene chloride the combined organic layer was washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure. The residue was chromatographed on silica (dichloromethane: ethyl acetate. 1:1) yielding 0.58 g 60% of the title compound.

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture was refluxed for 3 h under under nitrogen
  3. extractionAfter extraction with 2×50 ml of methylene chloride the combined organic layer
  4. washwas washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was chromatographed on silica (dichloromethane: ethyl acetate. 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-510b5e6461af464a9e5ca7953118173c
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06579884B1

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