Acetic Acid → 4-Chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(pyrrolidin-1-ylmethyl)indol-2-yl]isoindolinone

HRID 21318

Reaktionsgleichung

Reaktionsgleichung von HRID 21318
[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:9][C:8]([C:23]2[N:24]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:25]3[C:30]([CH:31]=2)=[CH:29][C:28]([CH:32]=O)=[CH:27][CH:26]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:41].[NH:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:21])([CH3:20])[CH3:22])([CH3:17])[CH3:18])=[CH:9][C:8]([C:23]2[N:24]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[C:25]3[C:30]([CH:31]=2)=[CH:29][C:28]([CH2:32][N:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)=[CH:27][CH:26]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:41]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 866283314-Chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Produkt 1

HCID 684921454-Chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(pyrrolidin-1-ylmethyl)indol-2-yl]isoindolinoneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Step 2 of Example 6, 4-chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (71.8 mg, 0.120 mmol) was dissolved in acetonitrile (2.5 mL), and the solution was treated with pyrrolidine (0.100 mL, 1.198 mmol), acetic acid (0.069 mL, 1.198 mmol) and sodium triacetoxyborohydride (76.3 mg, 0.360 mmol), followed by purification by flash column chromatography (chloroform/methanol=19/1, 4/1) to obtain 4-chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(pyrrolidin-1-ylmethyl)indol-2-yl]isoindolinone (51.4 mg, yield 66%).

Aufarbeitung

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=19/1, 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-f87bd281c4a94fe3a6765883725e93c4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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