Acetic Acid → 4-Hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(diethylaminomethyl)indol-2-yl]isoindolinone

HRID 21283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 21283
[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([C:13]2[N:14]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([CH:22]=O)=[CH:17][CH:16]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:31].[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([C:13]2[N:14]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([CH2:22][N:34]([CH2:35][CH3:36])[CH2:32][CH3:33])=[CH:17][CH:16]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:31]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8021DiethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866282994-Hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Produkt 1

HCID 684884364-Hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(diethylaminomethyl)indol-2-yl]isoindolinoneAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Step 2 of Example 6, 4-hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (0.415 g, 0.985 mmol) was dissolved in acetonitrile (16.0 mL), and the solution was treated with diethylamine (2.04 mL, 19.7 mmol), acetic acid (1.10 mL, 19.7 mmol) and sodium triacetoxyborohydride (0.626 g, 2.96 mmol) to obtain 4-hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(diethylaminomethyl)indol-2-yl]isoindolinone (0.202 g, 43%).

Quellen und Nachweise

ORD-Eintrag
ord-b2df79133cb44cdf9add076df7f59722
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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