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

HRID 547332Notes

Reaction equation

HRID 547332 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][C:6]1[N:7]([CH2:19][C:20]([CH3:23])([OH:22])[CH3:21])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1.[CH:24]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH2:25].O>O1CCCC1>[CH3:3][O:4][CH2:5][C:6]1[N:7]([CH2:19][C:20]([CH3:23])([O:22][CH2:25][CH2:24][S:26]([CH3:29])(=[O:28])=[O:27])[CH3:21])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 15224447alpha,alpha-Dimethyl-2-methoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

Product 1

HCID 672036312-(methoxymethyl)-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolineYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil, 59 mg, 1.47 mmol) was added to a stirred solution of 1-[2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (4.20 g, 14.7 mmol) in tetrahydrofuran (59 mL). After 5 minutes, methyl vinyl sulfone (3.10 g, 29.4 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 17 hours. Water (5 mL) was added and the mixture was concentrated under reduced pressure to afford an oil that was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to provide 3.7 g of 2-(methoxymethyl)-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline as a white solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto afford an oil that
  3. customwas purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f6f407f51e484098b02114ff59589ef8
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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