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Sodium Carbonate → 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone

HRID 394056
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Reaktionsgleichung

Reaktionsgleichung von HRID 394056
Br[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:22])[N:7]2[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21].[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.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>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[N:7]1[C:8]2[C:3](=[C:2]([C:27]3[CH:26]=[CH:25][C:24]([F:23])=[CH:29][C:28]=3[F:30])[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=2)[CH2:4][CH2:5][C:6]1=[O:22]
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Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 226479975-Bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone2×

Produkt 1

HCID 226480981-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 702EthanolLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A A mixture of 24 mg of 5-bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone (INTERMEDIATE 1), 28 mg of 2,4-difluorophenylboronic acid, 3 mg of Pd(Ph3P)4, and 0.15 mL of a 1M aqueous Na2CO3 solution in 2 mL of toluene and 0.2 mL of EtOH in a 10 mL flask equipped with a reflux condenser was evacuated and purged three times with Ar. The mixture was heated to reflux and stirred at this temperature for 3.5 h, then cooled and diluted with 15 mL EtOAc and 10 mL of saturated aqueous NaHCO3. The phases were separated and the organic phase was dried over MgSO4 and concentrated. The resulting residue was purified by preparative thin-layer chromatography, eluting with 3:1 hexanes-EtOAc, to yield 1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone. Mass spectrum (ESI) 434.0 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.50 (d, J=8.0 Hz, 2H); 7.35 (t, J=8.0 Hz, 1H), 7.32 (m, 1H); 6.96, (m, 2H); 6.52 (d, J=2.5 Hz, 1H); 5.89 (d, J=2.5 Hz, 1H); 3.69 (s, 3H); 2.64-3.00 (m, 4H).

Aufarbeitung

  1. customequipped with a reflux condenser
  2. customwas evacuated
  3. custompurged three times with Ar
  4. temperatureThe mixture was heated
  5. temperatureto reflux
  6. temperaturecooled
  7. additiondiluted with 15 mL EtOAc and 10 mL of saturated aqueous NaHCO3
  8. customThe phases were separated
  9. dry with materialthe organic phase was dried over MgSO4
  10. concentrationconcentrated
  11. customThe resulting residue was purified by preparative thin-layer chromatography
  12. washeluting with 3:1 hexanes-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-f2bcfde0dbfd4fee825367fa3ab90a91
Quelldatensatz
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06809199B2

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