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

HRID 21069

Reaktionsgleichung

Reaktionsgleichung von HRID 21069
[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].[NH2:30][CH:31]1[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[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+].[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]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Produkt 1

HCID 684890754-Chloro-7-[1-(tert-butoxycarbonyl)-5-(piperidin-4-ylaminomethyl)indol-2-yl]isoindolinoneAusbeute 194,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (34.5 mg, 0.0840 mmol) was dissolved in acetonitrile (1 mL), and the solution was treated with 4-amino-1-(tert-butoxycarbonyl)piperidine (70.1 mg, 0.350 mmol), acetic acid (0.100 mL, 1.74 mmol) and sodium triacetoxyborohydride (44.0 mg, 0.208 mmol). The reaction mixture was added with water and sodium carbonate to adjust the pH 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-(piperidin-4-ylaminomethyl)indol-2-yl]isoindolinone (80.8 mg).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cd8b6e1e99af4e1ea32745caf4838f35
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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