Potassium Carbonate → 3-[1-(benzyloxy)-1H-pyrrolo[3,2-b]pyridin-6-yl]-N,N-dimethylbenzamide

HRID 1404574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404574
[CH2:1]([O:8][N:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15](Br)[CH:16]=2)[CH:11]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:25][N:26]([CH3:38])[C:27]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)=[O:28]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[CH2:1]([O:8][N:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:33]3[CH:34]=[C:29]([CH:30]=[CH:31][CH:32]=3)[C:27]([N:26]([CH3:38])[CH3:25])=[O:28])[CH:16]=2)[CH:11]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27733923-(Dimethylcarbamoyl)benzeneboronic acidHCID 674577271-(benzyloxy)-6-bromo-1H-pyrrolo[3,2-b]pyridine

Produkt 1

HCID 462139453-[1-(benzyloxy)-1H-pyrrolo[3,2-b]pyridin-6-yl]-N,N-dimethylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-(benzyloxy)-6-bromo-1H-pyrrolo[3,2-b]pyridine (60 mg, 0.21 mmol, 1.0 eq), Pd(PPh3)4 (13 mg), 2.0 M K2CO3 (1.0 ml), DMF (1.2 ml), and [3-(dimethylcarbamoyl)phenyl]boronic acid (1.5 eq, 0.315 mmol) were reacted in microwave (110° C.) for 20 minutes. The upper layer was removed with a pipette and filtered, and purified with preparation HPLC to give the desired product.

Aufarbeitung

  1. customThe upper layer was removed with a pipette
  2. filtrationfiltered
  3. custompurified with preparation HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1c525d9490ac4ab2ad93348a13403001
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912330B2

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