Tributylphenyltin → 2-Cyclopropyl-7-methoxy-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17616

Reaktionsgleichung

Reaktionsgleichung von HRID 17616
Br[C:2]1[C:3]([O:17][CH3:18])=[C:4]2[O:8][C:7]([CH:9]3[CH2:11][CH2:10]3)=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14].C([Sn](CCCC)(CCCC)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)CCC.C(C1(C)C(O)=C(C(C)(C)C)C=CC1)(C)(C)C>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.O1CCOCC1>[CH:9]1([C:7]2[O:8][C:4]3[C:5](=[C:12]([C:15]#[N:16])[C:13]([CH3:14])=[C:2]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:3]=3[O:17][CH3:18])[N:6]=2)[CH2:11][CH2:10]1

Komponenten

6

Edukt 3

HCID 607632TributylphenyltinHCID 666371922,6-Di-t-butylcresolHCID 685847456-Bromo-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685848562-Cyclopropyl-7-methoxy-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under argon atmosphere, bis(triphenylphosphine)palladium(II) dichloride (777 mg, 1.11 mmol) was added to a 1,4-dioxane (110 ml) solution of 6-bromo-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile (I-83) (3.40 g, 11.1 mmol), tributylphenyltin (5.28 g, 14.4 mmol) and 2,6-di-tert-butylcresol (488 mg, 2.21 mmol), followed by stirring in an oil bath at 100° C. for 15 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was washed with diethyl ether to obtain the entitled compound (3.30 g, 98%) as a pale gray solid.

Aufarbeitung

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe insoluble matter was separated by filtration
  7. customthe residue obtained by concentration
  8. washwas washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-68507d3cc36e415e80c5a36e8ee390ba
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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