Chlorosuccinimide → 6'-Bromo-5'-chlorospiro[cyclopentane-1,3'-indolin]-2'-one

HRID 1619100

반응식

HRID 1619100 반응식
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[C:15](=[O:19])[NH:16]2)=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[C:15](=[O:19])[NH:16]2)=[CH:12][C:11]=1[Cl:1]

참가 물질

5

반응물 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 127170906'-Bromospiro[cyclopentane-1,3'-indolin]-2'-one

생성물 1

HCID 669540836'-Bromo-5'-chlorospiro[cyclopentane-1,3'-indolin]-2'-one수율 75.4%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

N-Chlorosuccinimide (0.50 g, 3.75 mmol) was added to a solution of 6′-bromospiro[cyclopentane-1,3′-indolin]-2′-one (preparation 2, 0.20 g, 0.75 mmol) in chloroform (5 mL). The mixture was stirred and heated to reflux. After 6 hours, the mixture was cooled to room temperature. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction and the mixture was extracted with chloroform. The organic layer was washed with brine, dried (MgSO4) and evaporated. Purification of the residue by flash chromatography (4:1 hexanes/ethyl acetate) gave the title compound (0.17 g, 75%) as a white solid.

후처리

  1. temperatureheated to reflux
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification of the residue by flash chromatography (4:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-45ada024ac554c368d201ecc32af279a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772288B2

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