Sodium hydride → 2-ethoxymethyl-1-{2-[2-(phenylsulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinoline

HRID 547295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547295
[H-].[Na+].[CH2:3]([O:5][CH2:6][C:7]1[N:8]([CH2:20][C:21]([CH3:24])([OH:23])[CH3:22])[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1)[CH3:4].[CH:25]([S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:29])=[O:28])=[CH2:26]>O1CCCC1>[CH2:3]([O:5][CH2:6][C:7]1[N:8]([CH2:20][C:21]([O:23][CH2:26][CH2:25][S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:28])=[O:29])([CH3:24])[CH3:22])[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1)[CH3:4]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 79664Phenyl vinyl sulfoneHCID 226726531-(2-(Ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Produkt 1

HCID 672029932-ethoxymethyl-1-{2-[2-(phenylsulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinolineAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Solid sodium hydride (30 mg of 60% dispersion in mineral oil, 0.72 mmol) was added to a stirred solution of 1-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (2.15 g, 7.2 mmol) and phenyl vinyl sulfone (2.42 g, 14.4 mmol) in anhydrous tetrahydrofuran (29 mL). The reaction mixture was stirred at ambient temperature for about 1 hour, and then it was quenched with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide crude product as an oil. This material was purified by column chromatography (silica gel eluting with 95/5 dichloromethane/methanol) to provide 0.95 g of 2-ethoxymethyl-1-{2-[2-(phenylsulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinoline as a colorless foam.

Aufarbeitung

  1. customit was quenched with water (50 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined extracts were washed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide crude product as an oil
  8. customThis material was purified by column chromatography (silica gel eluting with 95/5 dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-3e8e3d30ab744446852eba321bcc4c99
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939526B2

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