Methyl vinyl sulfone → 2-ethyl-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline
Reaction equation
[H-].[Na+].[CH2:3]([C:5]1[N:6]([CH2:18][C:19]([CH3:22])([OH:21])[CH3:20])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:4].[CH:23]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH2:24]>O1CCCC1.O>[CH2:3]([C:5]1[N:6]([CH2:18][C:19]([CH3:22])([O:21][CH2:24][CH2:23][S:25]([CH3:28])(=[O:27])=[O:26])[CH3:20])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:4]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Sodium hydride (60% dispersion in oil, 30 mg, 0.74 mmol) was added to a stirred solution of 1-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (2.00 g, 7.43 mmol) in tetrahydrofuran (30 mL). After five minutes, methyl vinyl sulfone (1.60 g, 14.9 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 1.5 hours and a solid formed. A few drops of water were added to the mixture, which was then concentrated under reduced pressure to yield a solid that was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to provide 1.90 g of 2-ethyl-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline as a white solid.
Workup
- customa solid formed
- concentrationwas then concentrated under reduced pressure
- customto yield a solid
- customthat was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-c5406f9396eb401682fc6b6bbf192f37
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939526B2
Reaction notes
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