ethyl 3-[(1E)-4-methoxybut-1-en-1-yl]imidazo[1,2-a]pyridine-2-carboxylate → Ethyl 3-(4-methoxybutyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylate

HRID 1509533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509533
[CH3:1][O:2][CH2:3][CH2:4]/[CH:5]=[CH:6]/[C:7]1[N:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[H][H]>C(OCC)(=O)C.[C].[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:10]2=[N:9][C:8]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Komponenten

5

Edukt 2

HCID 58355141ethyl 3-[(1E)-4-methoxybut-1-en-1-yl]imidazo[1,2-a]pyridine-2-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 58355371Ethyl 3-(4-methoxybutyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylateAusbeute 79,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 3-[(1E)-4-methoxybut-1-en-1-yl]imidazo[1,2-a]pyridine-2-carboxylate (1.40 g) was dissolved in ethyl acetate (30 ml), 10% palladium carbon (50% in water) (510 mg) was added and the mixture was stirred in a hydrogen stream at ambient temperature and normal pressure for 12 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-methanol (5:1) was concentrated under reduced pressure to give the object product (1.14 g).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washa fraction eluted with ethyl acetate-methanol (5:1)
  4. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6eaf296950fc4589ab07a60f11222507
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221836B2

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