Diisopropylethylamine → N-Phenyl-5-(2-(pyridin-4-yl)methylthiophenyl)-1,3,4-oxadiazol-2-amine

HRID 558173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558173
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:10][N:9]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(N(C(C)C)CC)(C)C.Cl.[N:72]1[CH:77]=[CH:76][C:75]([CH2:78][SH:79])=[CH:74][CH:73]=1>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[C:14]1([NH:13][C:11]2[O:12][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[S:79][CH2:78][C:75]3[CH:76]=[CH:77][N:72]=[CH:73][CH:74]=3)=[N:9][N:10]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 230938734-Pyridinemethanethiol hydrochlorideHCID 591525395-(2-bromophenyl)-N-phenyl-1,3,4-oxadiazol-2-amine

Produkt 1

HCID 24992355N-Phenyl-5-(2-(pyridin-4-yl)methylthiophenyl)-1,3,4-oxadiazol-2-amineAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A vessel containing 5-(2-bromophenyl)-N-phenyl-1,3,4-oxadiazol-2-amine (220 mg, 0.70 mmol; Reference Compound 7-(1)), tris(dibenzylideneacetone)dipalladium (33 mg, 0.035 mmol) and Xantphos (81 mg, 0.14 mmol) was replaced with nitrogen gas. To the vessel were added dioxane (5.0 mL), diisopropylethylamine (0.43 mL, 2.5 mmol) and 4-pyridinemethanethiol hydrochloride (210 mg, 1.3 mmol) successively at room temperature, and then the mixture was refluxed overnight. The reaction solution was cooled to room temperature and diluted with ethyl acetate (15 mL). The ethyl acetate solution was washed with a saturated brine solution (20 mL), dried over anhydrous sodium sulfate and concentrated under a reduced pressure. To the residue was added ethanol and a precipitated solid was filtered off and dried to give 180 mg (70%) of the titled compound as a pale brown solid.

Aufarbeitung

  1. temperaturethe mixture was refluxed overnight
  2. washThe ethyl acetate solution was washed with a saturated brine solution (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. additionTo the residue was added ethanol
  6. filtrationa precipitated solid was filtered off
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1f530c11d8ee4bd39eb35f4b5b3796c3
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063034B2

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