Dimethylformamide → HCID 67284590, Verbindung

HRID 1618654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618654
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[C:16]1([C:22](B2OC(C)(C)C(C)(C)O2)=[CH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CCOC(C)=O.[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH2:23])[C:11]=1[CH3:12]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 110316711-Phenylvinylboronic acid, pinacol esterHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Produkt 1

HCID 67284590HCID 67284590, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178478230HCID 178478230, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A screw cap vial was charged with 2,4-dichloro-5,7-difluoro-3-methylquinoline (99 mg, 0.398 mmol), 1-phenylvinylboronic acid pinacol ester (110 mg, 0.478 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium(II) (32.5 mg, 0.040 mmol), potassium carbonate (165 mg, 1.195 mmol), and DMF (3.98 mL), and the mixture was heated at 95° C. under a N2 atmosphere for 18 h. The reaction was then cooled to rt, diluted with EtOAc, and washed with water and brine. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with a gradient of 0-10% EtOAc in hexane to give 4-chloro-5,7-difluoro-3-methyl-2-(1-phenylvinyl)-quinoline as an orange solid. Mass Spectrum (ESI) m/e=316.0 (M+1).

Aufarbeitung

  1. customA screw cap vial
  2. temperatureThe reaction was then cooled to rt
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography
  7. washeluting with a gradient of 0-10% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-ffb918cefec943de9da1394f4ca252c6
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765940B2

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