Methanol → 1-Benzyl-2-methyl-5-(2,4-difluorophenyl)-1H-imidazole

HRID 250744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250744
[CH2:1]([N:8]1[C:12](Br)=[CH:11][N:10]=[C:9]1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].CO>CC([O-])=O.CC([O-])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd+2].COCCOC>[CH2:1]([N:8]1[C:12]([C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][C:20]=2[F:22])=[CH:11][N:10]=[C:9]1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 668687951-Benzyl-2-methyl-5-bromo-1H-imidazole

Produkt 1

HCID 668690851-Benzyl-2-methyl-5-(2,4-difluorophenyl)-1H-imidazoleAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 84538Palladium(2+) acetate--triphenylphosphane (1/2/2)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Heat a mixture of 1-benzyl-2-methyl-5-bromo-1H-imidazole (4.71 g, 18.7 mmol), 2,4-difluorophenyl boronic acid (6.92 g, 43.8 mmol), bis(acetato)bis(triphenylphosphine)palladium(II) (1.4 g, 1.875 mmol), 2M sodium carbonate (19 mL, 38 mmol), methanol (19 mL) and 1,2-dimethoxyethane (120 mL) to reflux for 18 hours. Cool to room temperature. Add water and ethyl acetate and separate layers. Dry organic layer over magnesium sulfate, filter, and concentrate under reduced pressure. Subject residue to silica gel chromatography, eluting with ethyl acetate/dichloromethane mixtures to give 3.59 g (12.6 mmol) of the desired compound.

Aufarbeitung

  1. temperatureHeat
  2. temperatureto reflux for 18 hours
  3. customAdd water and ethyl acetate and separate layers
  4. filtrationDry organic layer over magnesium sulfate, filter
  5. concentrationconcentrate under reduced pressure
  6. washSubject residue to silica gel chromatography, eluting with ethyl acetate/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-4dbd5cf5c4a7483c9599d0d9d0e461b4
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863310B2

Notizen zur Reaktion

Wird geladen…