Water → 4-Chloro-5-phenyl-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone

HRID 21311노트

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HRID 21311 반응식
[Cl:1][C:2]1[C:10](OS(C(F)(F)F)(=O)=O)=[CH:9][C:8]([C:19]2[N:20]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:23][CH:22]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:42].[C:43]1(B(O)O)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[F-].[Cs+].O>C(COC)OC>[Cl:1][C:2]1[C:10]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:9][C:8]([C:19]2[N:20]([C:35]([O:37][C:38]([CH3:40])([CH3:41])[CH3:39])=[O:36])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28][N:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)=[CH:23][CH:22]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:42]

참가 물질

6

반응물 4

HCID 962WaterHCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 866283294-Chloro-5-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone

생성물 1

HCID 684939564-Chloro-5-phenyl-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone수율 50.3%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

4-Chloro-5-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (100 mg, 0.159 mmol) was dissolved in dimethoxyethane (5.0 mL), and the solution was added with phenylboronic acid (58.2 mg, 0.478 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (10.4 mg, 0.0130 mmol) and cesium fluoride (145 mg, 0.954 mmol), followed by stirring at 90° C. for 6.0 hours under argon atmosphere. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=9/1) to obtain 4-chloro-5-phenyl-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (44.5 mg, yield 50%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=9/1)

출처 및 근거

ORD 기록
ord-bae33a7e710c491794ff54c19dc7844d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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