Water → 4-Chloro-5-(3-pyridylmethoxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone

HRID 21319

Reaktionsgleichung

[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([C:12]2[N:13]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:16][CH:15]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:35].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[N:43]1[CH:48]=[CH:47][CH:46]=[C:45]([CH2:49]Cl)[CH:44]=1.O>C(#N)C>[Cl:1][C:2]1[C:10]([O:11][CH2:49][C:45]2[CH:44]=[N:43][CH:48]=[CH:47][CH:46]=2)=[CH:9][C:8]([C:12]2[N:13]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:16][CH:15]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:35]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

4-Chloro-5-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (70.0 mg, 0.141 mmol) was suspended in acetonitrile (3.5 mL), and the suspension was added with cesium carbonate (91.9 mg, 0.282 mmol) and 3-pyridylmethyl chloride hydrochloride (23.1 mg, 0.141 mmol), followed by stirring at 50° C. for 12 hours under nitrogen atmosphere. The reaction mixture was added with water. The obtained solid was collected by filtration and washed with water, followed by drying under reduced pressure to obtain 4-chloro-5-(3-pyridylmethoxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (49.7 mg, yield 60%).

Aufarbeitung

filtrationThe obtained solid was collected by filtration
washwashed with water
customby drying under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-dbf0429802e34d3c8818abb3460bdbe6
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745641B2

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