Water → 6-methyl-1-(1-methylethyl)-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 1044261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044261
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1S(C)(=O)=O.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:26]3=[N:27][CH:28]=[C:29]([CH3:31])[CH:30]=[C:25]3[N:24]([CH:32]([CH3:34])[CH3:33])[C:23]2=[O:35])=[CH:18][CH:17]=1.[H-].[Na+].O>CN(C=O)C>[CH3:31][C:29]1[CH:30]=[C:25]2[N:24]([CH:32]([CH3:33])[CH3:34])[C:23](=[O:35])[N:22]([C:19]3[CH:18]=[CH:17][C:16]([O:15][C:3]4[N:2]([CH3:1])[C:6]5=[N:7][CH:8]=[CH:9][CH:10]=[C:5]5[N:4]=4)=[CH:21][CH:20]=3)[C:26]2=[N:27][CH:28]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 585773713-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 58577676HCID 58577676, Verbindung

Produkt 1

HCID 547710956-methyl-1-(1-methylethyl)-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (198 mg) and 3-(4-hydroxyphenyl)-6-methyl-1-(1-methylethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (177 mg) in DMF (1.5 mL) was added NaH (40.0 mg), and the mixture was stirred at 100° C. for 1 h. The mixture was heated at 180° C. for 30 min under microwave irradiation. The mixture was poured into water, and the mixture was extracted with EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, EtOAc/hexane) to give the title compound (125 mg) as white crystals.

Aufarbeitung

  1. temperatureThe mixture was heated at 180° C. for 30 min under microwave irradiation
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d0dc6061bc7d4d58832384fb1774178f
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563575B2

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