Sodium cyanoborohydride → HCID 17872261, Verbindung

HRID 1386070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386070
[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]([CH2:24][CH3:25])[C:17]=1[CH:18]=O)[CH3:15].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:24]([C:20]1[CH:21]=[CH:22][CH:23]=[C:16]([CH2:14][CH3:15])[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)[CH3:25]

Komponenten

6

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 131847782,6-DiethylbenzaldehydeHCID 226726328-Amino-2,3,6-trimethylimidazo[1,2-a]pyridine

Produkt 1

HCID 17872261HCID 17872261, VerbindungAusbeute 46,7 %

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), 2,6-diethylbenzaldehyde (0.7 g, 4.3 mmol) and zinc(II)chloride (0.44 g, 3 mmol) in 50 ml methanol was treated with sodium cyanoborohydride (0.19 g, 3 mmol) and then 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 silica gel with dichloromethylene first and then dichloromethylene:ethylacetate (1:1) which yielded 0.42 g 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 silica gel with dichloromethylene first

Quellen und Nachweise

ORD-Eintrag
ord-f6d2bd4e985f4d658fd6b9b2ca12a52f
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265415B1

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