Ethyl bromoacetate → (6-Chloro-3-methanesulfonyl-indol-1-yl)-acetic acid ethyl ester

HRID 23384ノート

反応式

HRID 23384 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN1CCCC1=O>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[C:6]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7]1)[CH3:23]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 225739526-Chloro-3-methanesulfonyl-1H-indole

生成物 1

HCID 20756837(6-Chloro-3-methanesulfonyl-indol-1-yl)-acetic acid ethyl ester収率 78.8%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
0 °C

実験手順

6-Chloro-3-methanesulfonyl-1H-indole (1.35 g, 5.88 mmole) was dissolved in anhydrous N-methylpyrrolidin-2-one (15 ml), cooled to 0° C. and placed under a nitrogen atmosphere. Sodium hydride (60% in oil, 0.28 g, 7 mmole) was added all at once and the mixture was stirred until the evolution of gas ceased (ca. 20-30 minutes). Ethyl bromoacetate (1.08 g, 6.47 mmole) was added all at once and the mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water, the organic layer was washed three times with water, dried over magnesium sulfate, filtered, and evaporated to dryness. The crude material thus obtained was purified by chromatography on silica gel, eluting with ethyl acetate-hexane (1:9) to (4:6) to afford 1.463 g of (6-chloro-3-methanesulfonyl-indol-1-yl)-acetic acid ethyl ester.

後処理

  1. custom(ca. 20-30 minutes)
  2. stirringwas stirred for 30 minutes
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washthe organic layer was washed three times with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude material thus obtained
  9. customwas purified by chromatography on silica gel
  10. washeluting with ethyl acetate-hexane (1:9) to (4:6)

出典と根拠

ORDレコード
ord-a7f9cf999999406c94a48cfc03fc066f
出典データセット
uspto-grants-2005_02
特許番号
US06852726B2

反応ノート

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