Sodium Carbonate → 7-[2-{6-(4-Methoxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-azepan-2-one

HRID 1710382

Reaktionsgleichung

Reaktionsgleichung von HRID 1710382
[C:1]1([C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([CH2:16][CH2:17][CH:18]4[NH:24][C:23](=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19]4)[NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1C=C2N=C(CCC3N[C:43](=[O:45])CCCC3)NC2=NC=1.C(=O)([O-])[O-].[Na+].[Na+].COC1C=CC(B(O)O)=CC=1>>[CH3:43][O:45][C:4]1[CH:3]=[CH:2][C:1]([C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([CH2:16][CH2:17][CH:18]4[NH:24][C:23](=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19]4)[NH:13][C:10]3=[N:11][CH:12]=2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 4

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 178516005HCID 178516005, Verbindung2×HCID 178516006HCID 178516006, Verbindung2×

Produkt 1

HCID 1784887447-[2-{6-(4-Methoxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-azepan-2-one

Versuchsvorschrift

The title compound is synthesized as described for 7-[2-(6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one (compound B1) from 100 mg of 7-[2-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one (compound C1), 677 μl of aqueous sodium carbonate solution (strength 2.0 M), 52 mg of commercially available 4-methoxyphenylboronic acid, and 72 mg of trans-dichloro-bis(tricyclohexyl-phosphine)-palladium(II) at 110° C. for 96 hours. Purification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-20 vol. % ethanol) yields 99 mg of the title compound as a waxy solid. ESI-MS: 365.2 (MH+). TLC: Rf=0.32 (dichloromethane/ethanol 10:1 parts by volume).

Aufarbeitung

  1. customThe title compound is synthesized
  2. customPurification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-20 vol. % ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-051ea964bfde4e308c726653b5d910d1
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790710B2

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