Sodium cyanoborohydride → 8-(2-Ethyl-6-methylbenzylamino)-2,3,6-trimethylimidazo[1,2-a]pyridine

HRID 1386071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386071
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH:18]=O)[CH3:15].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH2:18][NH:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1)[CH3:15]

Komponenten

6

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 226726328-Amino-2,3,6-trimethylimidazo[1,2-a]pyridineHCID 229974692-Ethyl-6-methylbenzaldehyde

Produkt 1

HCID 217173628-(2-Ethyl-6-methylbenzylamino)-2,3,6-trimethylimidazo[1,2-a]pyridineAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A stirred mixture of 8-amino-2,3,6-trimethylimidazo[1,2-a]pyridine (0.5 g, 2.8 mmol), 2-ethyl-6-methylbenzaldehyde (0.45 g, 3 mmol) and zinc(II)chloride (0.4 g, 3 mmol) in 50 ml methanol was treated with sodium cyanoborohydride (0.19 g, 3 mmol) and refluxed for 20 h. The methanol was evaporated under reduced pressure and the residue was dissolved in dichloromethylene and water. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The residue was chromatographed on silicagel with dichloromethylene:methanol (10:1) which yielded 0.28 g (33%) of the title compound.

Aufarbeitung

  1. temperaturerefluxed for 20 h
  2. customThe methanol was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethylene
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silicagel with dichloromethylene:methanol (10:1) which

Quellen und Nachweise

ORD-Eintrag
ord-d0cff468a59141b48036f99aff1afe30
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265415B1

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