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

HRID 23384노트

반응식

HRID 23384 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a7f9cf999999406c94a48cfc03fc066f
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852726B2

반응 노트

불러오는 중…