Triethylamine → 1-(2-methylpropyl)-2-propyl-7-vinyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1818214

Reaktionsgleichung

Reaktionsgleichung von HRID 1818214
[CH2:1](N(CC)CC)[CH3:2].C([B-](F)(F)F)=C.[K+].Br[C:16]1[CH:17]=[CH:18][C:19]2[C:20]3[N:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:28]([CH2:34][CH2:35][CH3:36])=[N:27][C:21]=3[C:22]([NH2:26])=[N:23][C:24]=2[CH:25]=1.[OH-].[Na+]>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:32][CH:31]([CH3:33])[CH2:30][N:29]1[C:20]2[C:19]3[CH:18]=[CH:17][C:16]([CH:1]=[CH2:2])=[CH:25][C:24]=3[N:23]=[C:22]([NH2:26])[C:21]=2[N:27]=[C:28]1[CH2:34][CH2:35][CH3:36]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 219842607-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amineHCID 23679353Potassium vinyltrifluoroborate

Produkt 1

HCID 219844201-(2-methylpropyl)-2-propyl-7-vinyl-1H-imidazo[4,5-c]quinolin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

Triethylamine (3.0 equivalents), potassium vinyltrifluoroborate (1.0 equivalent) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.2 equivalent) were added to a solution of 7-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (1.0 equivalent) in n-propanol (30 ml/g). The reaction mixture was heated at reflux under a nitrogen atmosphere until it was complete (between four and 18 hours) and then poured into water (3 volumes). The pH of the mixture was monitored and adjusted to pH 12 with the addition of 10% aqueous sodium hydroxide if needed. The mixture was extracted with ethyl acetate, and the combined organic fractions were filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (eluting with chloroform:methanol in a gradient from 100:0 to 90:10), followed by recrystallization from acetonitrile to provide 1-(2-methylpropyl)-2-propyl-7-vinyl-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under a nitrogen atmosphere until it
  3. custom(between four and 18 hours)
  4. extractionThe mixture was extracted with ethyl acetate
  5. filtrationthe combined organic fractions were filtered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash column chromatography on silica gel (
  8. washeluting with chloroform
  9. custommethanol in a gradient from 100:0 to 90:10), followed by recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-26b75d503f0d4382b06cc48cf8cad176
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598382B2

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