Sodium Carbonate → HCID 20814970, Verbindung

HRID 896655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896655
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=1.Br[C:22]1[CH:23]=[C:24]([CH:32]([CH3:34])[CH3:33])[CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][CH:28]=[CH:27]2.C([O-])([O-])=O.[Na+].[Na+]>CN(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>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:22]2[CH:23]=[C:24]([CH:32]([CH3:34])[CH3:33])[CH:25]=[C:26]3[C:31]=2[N:30]=[CH:29][CH:28]=[CH:27]3)[CH:6]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 110977913-(2-Methoxy-2-oxoethyl)phenylboronic acid, pinacol esterHCID 218655558-Bromo-6-isopropyl-quinoline

Produkt 1

HCID 20814970HCID 20814970, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
21 °C

Versuchsvorschrift

A solution of [3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester from Step 2 (4 g, 14 mmol), 8-bromo-6-isopropylquinoline (3 g, 12 mmol), Na2CO3 (2M, 18 mL, 36 mmol) and Pd(PPh3)4 (692 mg, 0.6 mmol) in DMF (250 mL) was heated at 80° C. under N2 for 18 h. The resulting reaction mixture was cooled to 21° C. and diluted with water and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 80:20) provided the [3-(6-Isopropyl-quinolin-8-yl)-phenyl]-acetic acid methyl ester compound.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with hexane/ethyl acetate, 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-5b287d9b692446beb1cf3e469962ecf2
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919353B2

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