Triethylamine → 2-Chloro-4-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-pyridine

HRID 1984649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984649
[C:1]([C:3]1[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][O:6][C:7]=1[CH3:8])#[CH:2].[Cl:15][C:16]1[CH:21]=[C:20](I)[CH:19]=[CH:18][N:17]=1.C(N(CC)CC)C>CN(C)C=O.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>[Cl:15][C:16]1[CH:21]=[C:20]([C:2]#[C:1][C:3]2[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:5][O:6][C:7]=2[CH3:8])[CH:19]=[CH:18][N:17]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 15165112-Chloro-4-iodopyridineHCID 534346474-Ethynyl-5-methyl-3-phenyl-isoxazole

Produkt 1

HCID 866169062-Chloro-4-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-pyridineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 4-ethynyl-5-methyl-3-phenyl-isoxazole (110 mg, 0.60 mmol), 2-chloro-4-iodopyridine (172 mg, 0.72 mmol), triethylamine (209 μl, 1.50 mmol) and bis(triphenylphosphine)palladium(II) chloride (13 mg, 0.02 mmol) in N,N-dimethylformamide (1.2 mL) was evaporated and flushed with argon. Cuprous iodide (2 mg, 0.01 mmol) was added and the reaction mixture was stirred for 1.5 h at 90° C. before it was cooled to ambient temperature and separated between aqueous sodium hydroxide (1 M, 20 mL) and ethyl acetate (30 mL). The aqueous layer was extracted with ethyl acetate (30 mL) and the combined organic layers were washed with aqueous sodium hydroxide (1 M, 20 mL), dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20) afforded the title compound (160 mg, 91%) as a colorless oil. MS: m/e=295.0/297.2 [M+H]+.

Aufarbeitung

  1. customwas evaporated
  2. customflushed with argon
  3. temperaturewas cooled to ambient temperature
  4. customseparated between aqueous sodium hydroxide (1 M, 20 mL) and ethyl acetate (30 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (30 mL)
  6. washthe combined organic layers were washed with aqueous sodium hydroxide (1 M, 20 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-3120cacd51d341689b9c70d64f733f4a
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544704B2

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