Triphenylphosphine → HCID 16113323, Verbindung

HRID 2240927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240927
[NH2:1][C:2]1[N:3]([CH3:25])[C:4](=[O:24])[C:5]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]([F:23])[F:22])=[CH:16][CH:15]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=2)[N:6]=1.[CH2:26](O)[CH2:27][CH:28]=[CH2:29].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[NH2:1][C:2]1[N:3]([CH3:25])[C:4](=[O:24])[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:29][CH2:28][CH:27]=[CH2:26])[CH:8]=2)([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]([F:22])[F:23])=[CH:16][CH:15]=2)[N:6]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 693893-Buten-1-olHCID 5462977Diethyl azodicarboxylateHCID 16112965HCID 16112965, Verbindung

Produkt 1

HCID 16113323HCID 16113323, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-amino-4-(4-(difluoromethoxy)phenyl)-4-(3-hydroxyphenyl)-1-methyl-1H-imidazol-5(4H)-one (0.070 g, 0.20 mmol), but-3-en-1-ol (0.023 g, 0.32 mmol), and PS—PPh3 (0.145 g, 0.32 mmol, 2.2 mmol/g) in THF (2 mL) is added diethylazodicarboxylate (0.058 g, 0.38 mmol) in THF (0.5 mL) dropwise. The mixture is stirred at 60° C. for 4 h. The solution is cooled to RT and the PPh3 is filtered and washed with CH2Cl2 and MeOH. The solvent is removed, the remaining material is absorbed onto Celite and purified by Flash Chromatography (15:1 CH2CL2:MeOH) to yield 2-amino-4-(3-(but-3-enyloxy)phenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one (0.051 g, 73%) as an off white foam.

Aufarbeitung

  1. temperatureThe solution is cooled to RT
  2. filtrationthe PPh3 is filtered
  3. washwashed with CH2Cl2 and MeOH
  4. customThe solvent is removed
  5. customthe remaining material is absorbed onto Celite
  6. custompurified by Flash Chromatography (15:1 CH2CL2:MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-92fd30dfb8624832be34a8346acd06c0
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723368B2

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