Methanol → HCID 66869085, Verbindung

HRID 729996

Reaktionsgleichung

Reaktionsgleichung von HRID 729996
[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 66869085HCID 66869085, VerbindungAusbeute 67,5 %

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), 2N Na2CO3 (19 mL, 38 mmol), MeOH (19 mL) and 1,2-dimethoxyethane (120 mL) to reflux for 18 h. Cool to RT. Add water and EtOAc and separate the layers. Dry organic layer over MgSO4, filter, and concentrate. Purify the residue (silica gel chromatography, eluting with EtOAc:CH2Cl2 mixtures) to give the desired compound (3.59 g).

Aufarbeitung

  1. temperatureHeat
  2. temperatureto reflux for 18 h
  3. customAdd water and EtOAc and separate the layers
  4. filtrationDry organic layer over MgSO4, filter
  5. concentrationconcentrate
  6. customPurify
  7. washthe residue (silica gel chromatography, eluting with EtOAc:CH2Cl2 mixtures)

Quellen und Nachweise

ORD-Eintrag
ord-663562bcc74b4a6da309af86daf84192
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582652B2

Verknüpfte Notizen

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