6-Chloroindoline-2,3-dione → Rac-6-chloro-3-(3,5-dimethoxy-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one

HRID 2102707노트

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HRID 2102707 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Cl:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18](=[O:24])[C:19](=[O:23])[NH:20]2)=[CH:16][CH:15]=1>O1CCCC1>[Cl:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=3)([OH:24])[C:19](=[O:23])[NH:20]2)=[CH:16][CH:15]=1

참가 물질

4

반응물 2

HCID 2413316-Chloroindoline-2,3-dioneHCID 178493477HCID 178493477, 화합물

생성물 1

HCID 57803060Rac-6-chloro-3-(3,5-dimethoxy-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-25 °C

실험 절차

A solution of 3,5-dimethoxyphenyl magnesium bromide in tetrahydrofuran (1.0 M, 6.9 mmol) (Aldrich) was added dropwise with magnetic stirring to a suspension of 6-chloroisatin (0.5 g, 2.76 mmol) in tetrahydrofuran (14 mL) under argon with cooling in a −25° C. bath at such a rate that reaction temperature was kept below −10° C. Cooling bath was then removed and mixture was allowed to warm to room temperature. After stirring for an additional 2 hours, 15% aqueous ammonium chloride solution and water were added and mixture extracted with ethyl acetate. Ethyl acetate layers were then washed with water, brine, combined, dried (Na2SO4), filtered and concentrated. Residue was stirred in dichloromethane at room temperature for 15 minutes and filtered to give crude rac-6-chloro-3-(3,5-dimethoxy-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one as an off-white powder. This was used in the next step without further purification.

후처리

  1. customthat reaction temperature
  2. customwas kept below −10° C
  3. temperatureCooling bath
  4. customwas then removed
  5. temperatureto warm to room temperature
  6. addition15% aqueous ammonium chloride solution and water were added
  7. extractionmixture extracted with ethyl acetate
  8. washEthyl acetate layers were then washed with water, brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. stirringResidue was stirred in dichloromethane at room temperature for 15 minutes
  13. filtrationfiltered

출처 및 근거

ORD 기록
ord-0e1b8f544eea48b59acd86591cc5141b
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576082B2

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