Potassium Fluoride → HCID 68958235, Verbindung

HRID 269389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269389
Cl[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:16]=[C:15]1B(O)O.[F-].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1COCC1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:16]=[C:15]1[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Komponenten

8

Edukt 4

HCID 522689Potassium FluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 2776266Benzo[b]furan-2-boronic acidHCID 134045925-Chloro-8-methoxyquinoline

Produkt 1

HCID 68958235HCID 68958235, VerbindungAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-chloro-8-methoxy-quinoline (0.330 g, 1.70 mmol) in THF (2 mL) at room temperature was added benzofuran-2-boronic acid (0.413 g, 2.55 mmol) followed by KF (0.296 mL, 5.10 mmol), Pd(OAc)2 (0.0382 g, 0.170 mmol), and 2-(di-tert-butyl phosphino)biphenyl (0.101 g, 0.340 mmol). The reaction mixture was stirred at room temperature for 18 hours and then diluted with EtOAc (200 mL). The organic layer was washed with H2O (20 mL) and brine (20 mL) then dried (Na2SO4). After concentration, the residue was purified on a Biotage Flash 40 apparatus (30-70% EtOAc:petroleum ether) to afford the product (0.291 g, 62%) as a solid. Mass spectrum (+ESI, [M+H]+) m/z 276. 1H NMR (500 MHz, DMSO-d6): δ 8.94 (d, 1H, J=2.2 Hz), 8.83 (d, 1H, J=9.4 Hz), 7.99 (d, 1H, J=8.6 Hz), 7.66-7.77 (m, 3H), 7.27-7.41 (m, 4H), and 4.6 ppm (s, 3H).

Aufarbeitung

  1. washThe organic layer was washed with H2O (20 mL) and brine (20 mL)
  2. dry with materialthen dried (Na2SO4)
  3. concentrationAfter concentration
  4. customthe residue was purified on a Biotage Flash 40 apparatus (30-70% EtOAc:petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-766455aae57e44d0a4de7d78f6ab2011
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446201B2

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