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Potassium Carbonate → 4-(benzyloxy)-6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridine

HRID 2209000
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2209000
[CH2:1]([O:8][C:9]1[C:14]2[N:15]([CH3:18])[CH:16]=[N:17][C:13]=2[CH:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O-:23])([O-])=O.[K+].[K+].COOB([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)OOC.[C:39]([O-])(O)=[O:40].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CCOC(C)=O.O.CC(O)C.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:14]2[N:15]([CH3:18])[CH:16]=[N:17][C:13]=2[CH:12]=[C:11]([C:36]2[CH:35]=[CH:34][C:33]([O:40][CH3:39])=[C:38]([O:23][CH3:20])[CH:37]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 208206864-Benzyloxy-6-chloro-3-methyl-imidazo[4,5-c]pyridineHCID 86637092Dimethoxyphenyl boronic acid

Produkt 1

HCID 1178430324-(benzyloxy)-6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel
HCID 3776IsopropanolLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 4-(benzyloxy)-6-chloro-3-methyl-3H-imidazo[4,5-c]pyridine 2.25 (0.54 g, 1.97 mmol), K2CO3 (0.68 g, 4.93 mmol), Pd(dppf)Cl2 (0.07 g, 0.1 mmol), and dimethoxy phenyl boronic acid (0.65 g, 3.55 mmol) under N2 was added toluene, iPrOH, and water (2:1:1, 10 mL), and the reaction was heated to 100° C. for 5 hrs. The reaction was cooled and EtOAc (40 mL)/NaHCO3 (20 mL) were added, the layers were separated and the aqueous was extracted with EtOAc (2×25 mL). The combined organics were washed with brine (50 mL), dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (EtOAc 0-->5% MeOH gradient) to afford 4-(benzyloxy)-6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridine 2.26.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customthe layers were separated
  3. extractionthe aqueous was extracted with EtOAc (2×25 mL)
  4. washThe combined organics were washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (EtOAc 0-->5% MeOH gradient)

Quellen und Nachweise

ORD-Eintrag
ord-30f13ea621c94cadaf261a85cfd8ad07
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09376441B2

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