Sodium Carbonate → Methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

HRID 394210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394210
Br[C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:24])[N:7]2[C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.CCOCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:24])[N:7]2[C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 22648178Methyl 5-bromo-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

Produkt 1

HCID 22648161Methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Methyl 5-bromo-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate (80 mg), 2-chlorophenylboronic acid (58 mg), palladium tetrakis(triphenylphosphine) (22 mg) and 1M aqueous sodium carbonate (450 μL) were mixed in ethylene glycol dimethyl ether (2 mL), degassed with argon and then heated to reflux for 90 min. The cooled reaction mixture was diluted with ether, filtered through celite and concentrated. The residue was purified by silica gel chromatography eluting with 70% hexane:30% ethyl acetate to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.82 (d, J=1.4 Hz, 1H); 7.65-7.39 (m, 8H); 7.23 (s, 1H); 6.82 (d, J=9.9 Hz, 1H), 3.90 (s, 3H). Mass spectrum: m/z 458 (M+H).

Aufarbeitung

  1. customdegassed with argon
  2. temperatureheated
  3. temperatureto reflux for 90 min
  4. customThe cooled reaction mixture
  5. filtrationfiltered through celite
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 70% hexane

Quellen und Nachweise

ORD-Eintrag
ord-331c3a6a4ac0434da8b432bfa725c16b
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809199B2

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