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Acetic Acid → 4-Chloro-7-[1-(tert-butoxycarbonyl)-5-(4-methylpiperidinomethyl)indol-2-yl]isoindolinone

HRID 21030
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HRID 21030 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=O)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].[CH3:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(#N)C.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:34]2[CH2:35][CH2:36][CH:31]([CH3:30])[CH2:32][CH2:33]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 693814-MethylpiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

생성물 1

HCID 684885904-Chloro-7-[1-(tert-butoxycarbonyl)-5-(4-methylpiperidinomethyl)indol-2-yl]isoindolinone
수율 51%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (41.0 mg, 0.0998 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with 4-methylpiperidine (0.048 mL, 0.41 mmol), acetic acid (0.345 mL, 6.03 mmol) and sodium triacetoxyborohydride (169 mg, 0.797 mmol). The reaction mixture was added with water and sodium hydrogen carbonate to adjust the pH of to 9. The mixture was 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 to obtain 4-chloro-7-[1-(tert-butoxycarbonyl)-5-(4-methylpiperidinomethyl)indol-2-yl]isoindolinone (25.0 mg, yield 51%).

후처리

  1. extractionThe mixture was extracted 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

출처 및 근거

ORD 기록
ord-ca602dcd24194675a124078124bfc4e9
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745641B2

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