1-methyl-2-(tributylstannyl)-1H-pyrrole → 7-fluoro-5-methyl-2-(1-methyl-1H-pyrrol-2-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17435

Reaktionsgleichung

Reaktionsgleichung von HRID 17435
C([Sn]([C:14]1[N:15]([CH3:19])[CH:16]=[CH:17][CH:18]=1)(CCCC)CCCC)CCC.C(C1(C)C(O)=C(C(C)(C)C)C=CC1)(C)(C)C.Cl[C:37]1[O:38][C:39]2[C:40](=[C:42]([C:54]#[N:55])[C:43]([CH3:53])=[C:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:45]=2[F:46])[N:41]=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.C1(C)C=CC=CC=1>[F:46][C:45]1[C:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[C:43]([CH3:53])[C:42]([C:54]#[N:55])=[C:40]2[C:39]=1[O:38][C:37]([C:14]1[N:15]([CH3:19])[CH:16]=[CH:17][CH:18]=1)=[N:41]2

Komponenten

6

Edukt 3

HCID 27693971-methyl-2-(tributylstannyl)-1H-pyrroleHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileHCID 666371922,6-Di-t-butylcresol

Produkt 1

HCID 510399657-fluoro-5-methyl-2-(1-methyl-1H-pyrrol-2-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Tributylstannyl-1-methylpyrrole (389 mg, 1.05 mmol), bis(triphenylphosphine)palladium(II) dichloride (49 mg, 0.07 mmol), and a catalytic amount of 2,6-di-tert-butylcresol (2 mg) were added to a toluene (20 ml) solution of 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (200 mg, 0.70 mol), followed by stirring under heat under nitrogen atmosphere for 3 hours. After cooling, the reaction liquid was filtered, and the solvent of the filtrate was evaporate away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and eluted with a mixed solvent of n-hexane/ethyl acetate (9:1, v/v→5:1, v/v) to obtain a main product. After washing with isopropyl ether, the entitled compound (50 mg, 22%) was collected by filtration as a pale yellow solid.

Aufarbeitung

  1. temperatureunder heat under nitrogen atmosphere for 3 hours
  2. temperatureAfter cooling
  3. customthe reaction liquid
  4. filtrationwas filtered
  5. customthe solvent of the filtrate was evaporate away under reduced pressure
  6. washeluted with a mixed solvent of n-hexane/ethyl acetate (9:1, v/v→5
  7. custom1, v/v) to obtain a main product
  8. washAfter washing with isopropyl ether
  9. filtrationthe entitled compound (50 mg, 22%) was collected by filtration as a pale yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-2d23f605678b474eaf1831fc88ee31f9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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