Sodium Carbonate → HCID 12043388, Verbindung

HRID 1059135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059135
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[N:14]=[CH:15][N:16]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=2)([OH:12])[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[F:37][C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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:38]1[CH:43]=[CH:42][C:41]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([C:13]3[N:14]=[CH:15][N:16]([C:18]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:17]=3)([OH:12])[CH:9]([CH3:10])[CH3:11])=[CH:4][CH:3]=2)=[CH:40][CH:39]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 120433871-(4-bromophenyl)-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol

Produkt 1

HCID 12043388HCID 12043388, VerbindungAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a suspension of 1-(4-bromophenyl)-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol (3.60 g), 4-fluorophenylboronic acid (1.50 g) and 2M aqueous sodium carbonate solution (26.8 ml) in dimethoxyethane (50 ml) was added tetrakis(triphenylphosphine)palladium(0) (387 mg). Under an argon atmosphere, the mixture was heated under reflux for 12 h. The reaction mixture was extracted with ethyl acetate-THF (8:3), washed with water and saturated brine, and dried. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chomatography (eluent, hexane:ethyl acetate=6:1→4:1) to give the title compound (3.16 g) as colorless needle crystals.

Aufarbeitung

  1. temperatureUnder an argon atmosphere, the mixture was heated
  2. temperatureunder reflux for 12 h
  3. extractionThe reaction mixture was extracted with ethyl acetate-THF (8:3)
  4. washwashed with water and saturated brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chomatography (eluent, hexane:ethyl acetate=6:1→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-1b2838f3ea2d4f4ca183791ef6802a69
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518257B1

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