Water → 7-bromo-2-ethoxymethyl-1-{2-[2-(methanesulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinoline

HRID 9413

Reaktionsgleichung

Reaktionsgleichung von HRID 9413
[CH:1]([S:3]([CH3:6])(=[O:5])=[O:4])=[CH2:2].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]([CH2:21][C:22]([CH3:25])([OH:24])[CH3:23])[C:19]([CH2:26][O:27][CH2:28][CH3:29])=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1.[H-].[Na+].O>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]([CH2:21][C:22]([O:24][CH2:2][CH2:1][S:3]([CH3:6])(=[O:5])=[O:4])([CH3:23])[CH3:25])[C:19]([CH2:26][O:27][CH2:28][CH3:29])=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 219840281-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Produkt 1

HCID 219844667-bromo-2-ethoxymethyl-1-{2-[2-(methanesulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl vinyl sulfone (3.0 g, 29 mmol) and 1-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (5.4 g, 14 mmol) in anhydrous THF (57 mL) was purged with nitrogen; solid sodium hydride (available as a 60% dispersion in mineral oil, 57 mg, 1.4 mmol) was added. The reaction was stirred for 70 minutes at ambient temperature, at which time an analysis by HPLC indicated a ratio of product to starting material of 3:1. The reaction mixture was combined with material from another run, and water (100 mL) was added. The aqueous layer was separated and extracted with ethyl acetate (100 mL, 50 mL). The combined organic fractions were washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol) to provide 7-bromo-2-ethoxymethyl-1-{2-[2-(methanesulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinoline.

Aufarbeitung

  1. additionwas added
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (100 mL, 50 mL)
  4. washThe combined organic fractions were washed with brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-4e57e73174c846a0ad0b36fef32f9e8b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091214B2

Verknüpfte Notizen

Wird geladen…