Potassium Carbonate → 3-(2-Ethoxyphenyl)-3-hydroxy-2-oxo-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indole-5-carbonitrile

HRID 219756

반응식

HRID 219756 반응식
C([O-])(C)(C)C.[K+].[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[C:12]2([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH2:27][CH3:28])[OH:19])#[N:8].[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][C:37]=2[S:39](Cl)(=[O:41])=[O:40])[CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[CH2:27]([O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:12]1([OH:19])[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([C:7]#[N:8])[CH:10]=2)[N:14]([S:39]([C:37]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:38]=2[N:29]=[CH:30][CH:31]=[CH:32]3)(=[O:40])=[O:41])[C:13]1=[O:18])[CH3:28]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 292208-Quinolinesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 665930415-Cyano-3-(2-ethoxyphenyl)-3-hydroxy-indol-2-one

생성물 1

HCID 690705533-(2-Ethoxyphenyl)-3-hydroxy-2-oxo-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indole-5-carbonitrile수율 68.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

2.3 g (10.6 mMol) of potassium tert-butanolate are added to 5.5 g (18.7 mMol) of the intermediate 1b in 40 ml of DMF at 0° C. The reaction mixture was stirred for 1 h. Then 4.25 g (18.7 mMol) of 8-quinolinesulfonyl chloride were added at 0° C. The reaction solution was stirred at 0° C. for three hours and then at room temperature for 16 h. This reaction solution was poured into aqueous K2CO3 solution, resulting in a precipitate which was isolated. This solid was dissolved in methylene chloride, dried and concentrated in vacuo. The resulting residue was recrystallized from ethanol. 6.2 g of the product were obtained.

후처리

  1. stirringThe reaction solution was stirred at 0° C. for three hours
  2. waitat room temperature for 16 h
  3. customresulting in a precipitate which
  4. customwas isolated
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-1271c5c5631b453f93aa8785d671661c
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202870B2

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