Sodium hydride → ethyl 2-[4-(1-ethyl-6-methyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenoxy]imidazo[1,2-a]pyridine-3-carboxylate

HRID 82645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82645
Cl[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH2:16]([N:18]1[C:26]2[C:21](=[N:22][CH:23]=[C:24]([CH3:27])[CH:25]=2)[N:20]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)[C:19]1=[O:35])[CH3:17].[H-].[Na+].C([O-])(O)=O.[Na+]>COCCOC>[CH2:16]([N:18]1[C:26]2[C:21](=[N:22][CH:23]=[C:24]([CH3:27])[CH:25]=2)[N:20]([C:28]2[CH:33]=[CH:32][C:31]([O:34][C:2]3[N:3]=[C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][N:5]4[C:10]=3[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:30][CH:29]=2)[C:19]1=[O:35])[CH3:17]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 21643308Ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylateHCID 585776031-ethyl-3-(4-hydroxyphenyl)-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Produkt 1

HCID 58577566ethyl 2-[4-(1-ethyl-6-methyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenoxy]imidazo[1,2-a]pyridine-3-carboxylateAusbeute 12,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The mixture of ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylate (504 mg), 1-ethyl-3-(4-hydroxyphenyl)-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (302 mg) and NaH (67.3 mg) in DME (4 mL) was heated at 50° C. for 1 h. The mixture was heated at 200° C. for 3 h under microwave irradiation. The mixture was poured into sat. NaHCO3, 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 (62.0 mg) as a white solid.

Aufarbeitung

  1. temperatureThe mixture was heated at 200° C. for 3 h 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-89d0ab99bb844c67b4997ec263974a67
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846713B2

Notizen zur Reaktion

Wird geladen…