Ethyl trimethylsilyl malonate → Ethyl 3-[2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)phenyl]-3-oxopropionate

HRID 749486노트

반응식

HRID 749486 반응식
C([Li])CCC.[C:6]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:7][C:8]([O:10][Si](C)(C)C)=O.[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[C:26]([NH:30][C:31]2[C:36]([F:37])=[CH:35][C:34]([F:38])=[CH:33][C:32]=2[Cl:39])=[CH:25][C:21]=1C(Cl)=O>CCCCCC.C(OCC)C.C(COC)OC.C(OCC)(=O)C>[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[C:26]([NH:30][C:31]2[C:36]([F:37])=[CH:35][C:34]([F:38])=[CH:33][C:32]=2[Cl:39])=[CH:25][C:21]=1[C:8](=[O:10])[CH2:7][C:6]([O:16][CH2:17][CH3:18])=[O:15]

참가 물질

8

반응물 3

HCID 87655Ethyl trimethylsilyl malonateHCID 866002582,4-Dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoyl chlorideHCID 178418339Butyllithium

생성물 1

HCID 68799347Ethyl 3-[2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)phenyl]-3-oxopropionate

시약·촉매·용매 4

HCID 3283Diethyl Ether용매HCID 8058Hexane용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-75 °C

실험 절차

1.4 ml of a 1.6 M solution of butyllithium in hexane was added to a solution of 3.47 g (17.0 mmol) of ethyl trimethylsilyl malonate in 45 ml of diethyl ether at −75° C. in such a way that the temperature did not rise above −60° C. The mixture was then stirred at −75° C. for 30 minutes. The 2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoyl chloride was dissolved in 45 ml of dimethoxyethane and added dropwise in 40 minutes. The mixture was slowly warmed to 10° C. and stirred at this temperature for 2.5 hours. The reaction mixture was diluted with ethyl acetate and washed twice each with 250 ml portions of water and saturated sodium bicarbonate solution. The organic phase was dried and concentrated. 3.88 g of the crude mixture were obtained and were reacted without further purification in the next stage.

후처리

  1. customdid not rise above −60° C
  2. additionadded dropwise in 40 minutes
  3. temperatureThe mixture was slowly warmed to 10° C.
  4. stirringstirred at this temperature for 2.5 hours
  5. washwashed twice each with 250 ml portions of water and saturated sodium bicarbonate solution
  6. customThe organic phase was dried
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-137ca073d3944f19b6d5b0a457ad8aa8
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402674B2

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