Water → 2-butyl-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline

HRID 547325Notes

Reaction equation

HRID 547325 reaction equation
[H-].[Na+].[CH2:3]([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)[CH2:4][CH2:5][CH3:6].[CH:25]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH2:26].O>O1CCCC1.[Cl-].[Na+].O>[CH2:3]([C:7]1[N:8]([CH2:20][C:21]([CH3:24])([O:23][CH2:26][CH2:25][S:27]([CH3:30])(=[O:29])=[O:28])[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)[CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 46831677HCID 46831677, compound

Product 1

HCID 672032042-butyl-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolineYield 48.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (60% dispersion in oil, 55 mg, 1.38 mmol) was added to a stirred solution of 1-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (4.10 g, 13.8 mmol) in tetrahydrofuran (55 mL). After 5 minutes, methyl vinyl sulfone (2.90 g, 27.6 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 1 hour. Water (50 mL) and a small amount of brine were added and the mixture was extracted with ethyl acetate (2×50 mL). The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford a solid that was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to provide 2.7 g of 2-butyl-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford a solid
  7. customthat was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e5d1c12a52f54f2a86ba68067a6d4335
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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