Methyl vinyl sulfone → 2-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclobutyl}methyl)-1H-imidazo[4,5-c]quinoline

HRID 547317Notes

Reaction equation

HRID 547317 reaction equation
N12CCCN=C1CCCCC2.[CH:12]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH2:13].[CH2:18]([O:20][CH2:21][C:22]1[N:23]([CH2:35][C:36]2([OH:40])[CH2:39][CH2:38][CH2:37]2)[C:24]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[CH:26][C:25]=2[N:34]=1)[CH3:19].[H-].[Na+]>O1CCCC1.O>[CH2:18]([O:20][CH2:21][C:22]1[N:23]([CH2:35][C:36]2([O:40][CH2:13][CH2:12][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:39][CH2:38][CH2:37]2)[C:24]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[CH:26][C:25]=2[N:34]=1)[CH3:19]

Participants

7

Reactant 4

HCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 575153931-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclobutanol

Product 1

HCID 672036362-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclobutyl}methyl)-1H-imidazo[4,5-c]quinolineYield 64.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.10 mL, 0.74 mmol) followed by methyl vinyl sulfone (1.60 g, 14.8 mmol) were added to a stirred solution of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclobutanol (2.30 g, 7.39 mmol) in tetrahydrofuran (30 mL). The reaction mixture was stirred at room temperature for 1 hour and a small amount of sodium hydride (60% dispersion in mineral oil) was added. Water (50 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford an oil that was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to provide 2.0 g of 2-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclobutyl}methyl)-1H-imidazo[4,5-c]quinoline as an oil.

Workup

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

Sources & evidence

ORD record
ord-8e82a50220e8444ebf8602b624123ac2
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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