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Potassium Carbonate → 5-Amino-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile

HRID 17525
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17525
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](Br)([CH3:15])[CH:4]([C:17]#[N:18])[C:3]=1[O:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.CB1OB(C)OB(C)O1>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([C:17]#[N:18])[C:5]([CH3:15])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]=1[F:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574072TrimethylboroxineHCID 685848335-Amino-2-bromo-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile

Produkt 1

HCID 860975095-Amino-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
2×
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

5-Amino-2-bromo-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile (I-235) (2.02 g, 6.29 mmol), potassium carbonate (2.61 g, 18.87 mmol) and tetrakis(triphenylphosphine)palladium(0) (727 mg, 0.63 mmol) were dissolved in 10% water-containing 1,4-dioxane (50 ml), and at room temperature, trimethylboroxine (50 wt. % tetrahydrofuran solution, 1.90 ml, 7.55 mmol) was added. After stirring under nitrogen atmosphere at 110° C. for 8 hours and then cooling to room temperature, tetrakis(triphenylphosphine)palladium(0) (727 mg, 0.63 mmol) was added, followed by further stirring at 110° C. for 11 hours. After cooling to room temperature, the insoluble matter was separated by filtration, the filtrate was fractionated with ethyl acetate and saturated brine. The organic layer was separated, the aqueous layer was again extracted with ethyl acetate.

Aufarbeitung

  1. temperaturecooling to room temperature
  2. stirringby further stirring at 110° C. for 11 hours
  3. temperatureAfter cooling to room temperature
  4. customthe insoluble matter was separated by filtration
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was again extracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-41d3ba0b6a6148fcbd9992559d038a83
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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