Trimethyl orthovalerate → 7-bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinoline

HRID 9350

Reaktionsgleichung

Reaktionsgleichung von HRID 9350
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:18](OC)(OC)(OC)[CH2:19][CH2:20][CH2:21][CH3:22]>Cl.N1C=CC=CC=1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:18]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Komponenten

5

Edukt 2

HCID 83755Trimethyl orthovalerateHCID 688181597-bromo-N4-isobutylquinoline-3,4-diamine

Produkt 1

HCID 219843597-bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinolineAusbeute 43,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10176127Pyridinium chlorideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

7-Bromo-N4-isobutylquinoline-3,4-diamine (39.4 g of crude material), trimethyl orthovalerate (32 g, 0.20 mol), and pyridine hydrochloride (0.31 g, 2.7 mmol) were combined with anhydrous toluene (500 mL) and heated to reflux for 30 min. The reaction was cooled to room temperature, concentrated, and the residue was purified by chromatography on silica gel (75% ethyl acetate in hexane to 100% ethyl acetate gradient) to afford 21.2 g of 7-bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinoline as a yellow solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. concentrationconcentrated
  4. customthe residue was purified by chromatography on silica gel (75% ethyl acetate in hexane to 100% ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-162be3fc5e3f4ed98a5683cec7677ead
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091214B2

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