Acetic Acid → 4-Chloro-7-{1-(tert-butoxycarbonyl)-5-[4-(2-cyanoethyl)piperazin-1-ylmethyl]indol-2-yl}isoindolinone

HRID 21068

Reaktionsgleichung

Reaktionsgleichung von HRID 21068
[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].[C:30]([CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)#[N:31].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][N:37]2[CH2:38][CH2:39][N:34]([CH2:33][CH2:32][C:30]#[N:31])[CH2:35][CH2:36]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 20520503-(Piperazin-1-yl)propanenitrileHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Produkt 1

HCID 684897264-Chloro-7-{1-(tert-butoxycarbonyl)-5-[4-(2-cyanoethyl)piperazin-1-ylmethyl]indol-2-yl}isoindolinoneAusbeute 100 %

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 (40.8 mg, 0.0993 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with 1-(2-cyanoethyl)piperazine (59.8 mg, 0.430 mmol), acetic acid (0.115 mL, 2.01 mmol) and sodium triacetoxyborohydride (74.3 mg, 0.351 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-[4-(2-cyanoethyl)piperazin-1-ylmethyl]indol-2-yl}isoindolinone (53.0 mg, yield 100%).

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-623d57d13e384695bcab9dee732e33b4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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