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

HRID 1619100

反応式

HRID 1619100 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-45ada024ac554c368d201ecc32af279a
出典データセット
uspto-grants-2014_07
特許番号
US08772288B2

関連ノート

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