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

HRID 547320
ノート
印刷プレビュー

反応式

HRID 547320 の反応式
[H-].[Na+].[Cl:3][C:4]1[C:13]2[N:14]=[CH:15][N:16]([CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1.[CH:22]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH2:23]>O1CCCC1>[Cl:3][C:4]1[C:13]2[N:14]=[CH:15][N:16]([CH2:17][C:18]([CH3:21])([O:20][CH2:23][CH2:22][S:24]([CH3:27])(=[O:26])=[O:25])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 98384584-chloro-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

生成物 1

HCID 866134654-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (60% dispersion in mineral oil, 58 mg, 1.45 mmol) was added to a stirred solution of 1-(4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (described in U.S. Pat. No. 4,689,338 Example 189, Part D, 4.00 g, 14.5 mmol) in tetrahydrofuran (58 mL). After 5 minutes, methyl vinyl sulfone (3.10 g, 29.0 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 17 hours. The volatiles were removed under reduced pressure and the resulting oil was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to yield 4.3 g of 4-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline as a foam.

後処理

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting oil was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-22ff6cc8f5214c0586b5d4477e90b99b
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07939526B2

反応ノート

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