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

HRID 21014

Reaktionsgleichung

Reaktionsgleichung von HRID 21014
[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].[NH:30]([CH2:34][CH2:35][OH:36])[CH2:31][CH2:32][OH:33].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[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:30]([CH2:34][CH2:35][OH:36])[CH2:31][CH2:32][OH:33])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8113DiethanolamineHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Produkt 1

HCID 684908604-Chloro-7-(1-(tert-butoxycarbonyl)-5-[di(2-hydroxyethyl)aminomethyl]indol-2-yl)isoindolinoneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 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, 0.0922 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with diethanolamine (0.035 mL, 0.37 mmol), acetic acid (0.106 mL, 1.85 mmol) and sodium triacetoxyborohydride (98 mg, 0.46 mmol), followed by purification by preparative thin-layer chromatography (hexane/ethyl acetate=1/2) to obtain 4-chloro-7-(1-(tert-butoxycarbonyl)-5-[di(2-hydroxyethyl)aminomethyl]indol-2-yl)isoindolinone (29.2 mg, yield 64%).

Aufarbeitung

  1. customfollowed by purification by preparative thin-layer chromatography (hexane/ethyl acetate=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-ef82224e0ab342b3b88883e0807733d5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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