Potassium Carbonate → 2,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde

HRID 2212606

Reaktionsgleichung

Reaktionsgleichung von HRID 2212606
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:21])=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:10]=2)[C:5]([CH3:23])([CH3:22])[CH2:4][C:3]1=[O:24].Br[C:26]1[C:27]([F:37])=[C:28]([CH:31]=[C:32]([F:36])[C:33]=1[O:34][CH3:35])[CH:29]=[O:30].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)(=O)C.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>[F:37][C:27]1[C:26]([C:9]2[CH:10]=[C:11]3[C:6]([C:5]([CH3:22])([CH3:23])[CH2:4][C:3](=[O:24])[N:2]3[CH3:1])=[CH:7][C:8]=2[CH3:21])=[C:33]([O:34][CH3:35])[C:32]([F:36])=[CH:31][C:28]=1[CH:29]=[O:30]

Komponenten

9

Edukt 3

HCID 11430Potassium CarbonateHCID 219664313-Bromo-2,5-difluoro-4-methoxybenzaldehydeHCID 21966467HCID 21966467, Verbindung

Produkt 1

HCID 219664662,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1,4,4,6-tetramethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinoline-2-one (0.36 g, 1.1 mmol), 3-bromo-2,5-difluoro-4-methoxybenzaldehyde (example 13 a) (0.25 g, 0.1 mmol) and potassium carbonate (0.275 g, 1.99 mmol) in toluene (5 mL), ethanol (1 mL) and water (0.75 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) was added and the mixture heated at reflux under argon for 20 hrs. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (0%–20% ethyl acetate in hexane) to give 97 mg of 2,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde.

Aufarbeitung

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon for 20 hrs
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (0%–20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d2d5e6a394c041c89ee0859a93a0cc5d
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07102000B2

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