Methyl vinyl sulfone → 1-{2-[2-(methylsulfonyl)ethoxy]-2-methylpropyl}-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline
Reaction equation
[CH2:1]([O:3][CH2:4][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)[CH3:2].[CH:23]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH2:24]>>[CH3:28][S:25]([CH2:23][CH2:24][O:21][C:19]([CH3:22])([CH3:20])[CH2:18][N:6]1[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]=[C:5]1[CH2:4][O:3][CH2:1][CH3:2])(=[O:27])=[O:26]Participants
3
Procedure
Using the general method of Example 8 Part D, 1-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (2.0 g, 6.7 mmol) was reacted with methyl vinyl sulfone (1.42 g, 13.4 mmol). The reaction mixture 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 1.75 g of 1-{2-[2-(methylsulfonyl)ethoxy]-2-methylpropyl}-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline as a colorless foam.
Workup
- customThe reaction mixture was quenched with water (50 mL)
- extractionextracted with ethyl acetate (3×50 mL)
- washThe combined extracts were washed with brine (50 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customto provide crude product as an oil
- customThis material was purified by column chromatography (silica gel eluting with 95/5 dichloromethane/methanol)
Sources & evidence
- ORD record
- ord-8a3359aeca264f80ae79a84811aca6dd
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939526B2
Reaction notes
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