Stannane, tributyl(1-ethoxyethenyl)- → 6-(1-Ethoxyvinyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17439

Reaktionsgleichung

Reaktionsgleichung von HRID 17439
Br[C:2]1[C:3]([F:17])=[C:4]2[O:8][C:7]([N:9]([CH3:11])[CH3:10])=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14].C([Sn](CCCC)(CCCC)[C:23]([O:25][CH2:26][CH3:27])=[CH2:24])CCC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(C1(C)C(O)=C(C(C)(C)C)C=CC1)(C)(C)C>[CH2:26]([O:25][C:23]([C:2]1[C:3]([F:17])=[C:4]2[O:8][C:7]([N:9]([CH3:11])[CH3:10])=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14])=[CH2:24])[CH3:27]

Komponenten

6

Edukt 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 685849786-Bromo-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685855916-(1-Ethoxyvinyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrileAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 666371922,6-Di-t-butylcresolKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

6-Bromo-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-168) (0.80 g, 2.68 mmol) was dissolved in toluene (25 ml), then tributyl(1-ethoxyvinyl)tin (1.30 ml, 3.85 mmol), 2,6-di-tert-butylcresol (12 mg, 0.05 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.10 g, 0.14 mmol) were added followed by heating under reflux for 3 days. The insoluble matter was removed by filtration through Celite, followed by washing with ethyl acetate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:hexane=1:2 to 2:3 to 9:1 to dichloromethane:methanol=200:1) to obtain a brown solid (0.51 g, 66%).

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 3 days
  3. customThe insoluble matter was removed by filtration through Celite
  4. washby washing with ethyl acetate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (dichloromethane:hexane=1:2 to 2:3 to 9:1 to dichloromethane:methanol=200:1)

Quellen und Nachweise

ORD-Eintrag
ord-9295067eed32455cb27d4142ccdc3865
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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