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Potassium Carbonate → HCID 178494667, Verbindung

HRID 1488102
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1488102
I[C:2]1[NH:6][C:5]([CH2:7][O:8][CH3:9])=[N:4][C:3]=1[CH3:10].[CH3:11][C:12]1[CH:21]=[C:20]([CH3:22])[C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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]>[CH3:9][O:8][CH2:7][C:5]1[NH:6][C:2]([C:19]2[C:20]([CH3:22])=[CH:21][C:12]([CH3:11])=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])=[C:3]([CH3:10])[N:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 59224686Methyl 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate2×HCID 1784946745-Iodo-2-(methoxymethyl)-4-methyl-1H-imidazole2×

Produkt 1

HCID 178494667HCID 178494667, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Into a 50-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 5-iodo-2-(methoxymethyl)-4-methyl-1H-imidazole (compound 222.3, 400 mg, 1.59 mmol) in 1,4-dioxane (15 mL). Methyl 2,4-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (compound 160.1, 510 mg, 1.76 mmol), a solution of potassium carbonate (662 mg, 4.79 mmol) in water (1 mL) and Pd(dppf)Cl2 (234 mg, 0.32 mmol) were added to the reaction. The reaction mixture was stirred overnight at 90° C. The solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography with dichloromethane/ethyl acetate (1:1) as eluent to furnish 220 mg (48%) of the title compound as a yellow solid.

Aufarbeitung

  1. customInto a 50-mL three neck round-bottom flask, which was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customThe solids were removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography with dichloromethane/ethyl acetate (1:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-79779f827c8c49acb6f6e31217f8bb0f
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09428502B2

Notizen zur Reaktion

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