反応式
[CH:1]([S:3]([CH3:6])(=[O:5])=[O:4])=[CH2:2].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]([CH2:21][C:22]([CH3:25])([OH:24])[CH3:23])[C:19]([CH2:26][O:27][CH2:28][CH3:29])=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1.[H-].[Na+].O>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]([CH2:21][C:22]([O:24][CH2:2][CH2:1][S:3]([CH3:6])(=[O:5])=[O:4])([CH3:23])[CH3:25])[C:19]([CH2:26][O:27][CH2:28][CH3:29])=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
実験手順
A solution of methyl vinyl sulfone (3.0 g, 29 mmol) and 1-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (5.4 g, 14 mmol) in anhydrous THF (57 mL) was purged with nitrogen; solid sodium hydride (available as a 60% dispersion in mineral oil, 57 mg, 1.4 mmol) was added. The reaction was stirred for 70 minutes at ambient temperature, at which time an analysis by HPLC indicated a ratio of product to starting material of 3:1. The reaction mixture was combined with material from another run, and water (100 mL) was added. The aqueous layer was separated and extracted with ethyl acetate (100 mL, 50 mL). The combined organic fractions were washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol) to provide 7-bromo-2-ethoxymethyl-1-{2-[2-(methanesulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinoline.
後処理
- additionwas added
- customThe aqueous layer was separated
- extractionextracted with ethyl acetate (100 mL, 50 mL)
- washThe combined organic fractions were washed with brine (50 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol)
出典と根拠
- ORDレコード
- ord-4e57e73174c846a0ad0b36fef32f9e8b
- 出典データセット
- uspto-grants-2006_08
- 特許番号
- US07091214B2
関連ノート
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