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

HRID 21013

Reaktionsgleichung

Reaktionsgleichung von HRID 21013
[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][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]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]([CH3:27])([CH3:26])[CH3:28])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]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 4082852-MorpholinoethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Produkt 1

HCID 684924344-Chloro-7-(1-(tert-butoxycarbonyl)-5-[(2-morpholinoethyl)aminomethyl]indol-2-yl)isoindolinoneAusbeute 107,6 %

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 (37.6 mg, 0.0915 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with 4-(2-aminoethyl)morpholine (0.048 mL, 0.37 mmol), acetic acid (0.105 mL, 1.83 mmol) and sodium triacetoxyborohydride (97 mg, 0.46 mmol). The reaction mixture was added with water and sodium carbonate, followed by extracting with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to obtain 4-chloro-7-(1-(tert-butoxycarbonyl)-5-[(2-morpholinoethyl)aminomethyl]indol-2-yl)isoindolinone (51.7 mg).

Aufarbeitung

  1. extractionby extracting 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-2217f9356c7c43edbda4070bb5dcad82
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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