2-Iodopyridine → 2-(4-(3-(2-Methoxyphenyl)-1,2,4-oxadiazol-5-yl)but-1-ynyl)pyridine

HRID 1189087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1189087
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[N:13]=1)[CH2:9][C:10]#[CH:11]>C(N(CC)CC)C.[Cu](I)I.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>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]1[N:13]=[C:12]([CH2:8][CH2:9][C:10]#[C:11][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[O:16][N:15]=1

Komponenten

6

Edukt 2

HCID 2211262-IodopyridineHCID 860867965-(But-3-ynyl)-3-(2-methoxyphenyl)-1,2,4-oxadiazole

Produkt 1

HCID 115077712-(4-(3-(2-Methoxyphenyl)-1,2,4-oxadiazol-5-yl)but-1-ynyl)pyridineAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

In a dry reaction tube containing in suspension copper iodide (12 mg, 0.07 mmol) and triethylamine (4.1 mL, 29 mmol), were added 2-iodopyridine (139 μL, 1.3 mmol) and Pd(PPh3)2Cl2 (46 mg, 0.07 mmol) under N2. A yellow suspension is obtained and after a few minutes of stiffing at room temperature, was added a solution 5-(but-3-ynyl)-3-(2-methoxyphenyl)-1,2,4-oxadiazole (299 mg, 1.3 mmol) in triethylamine (0.7 mL) under N2. Immediately the color of the reaction turns to black. The mixture was stirred at room temperature for 20h under N2. Triethylamine was removed under reduce pressure and the crude product was purified by flash chromatography (Prepacked column 10 g, cyclohexane/AcOEt: from 60/40 to 50/50 as eluent) to afford 50 mg of 2-(4-(3-(2-methoxyphenyl)-1,2,4-oxadiazol-5-yl)but-1-ynyl)pyridine (13%) as brown oil.

Aufarbeitung

  1. customIn a dry reaction tube
  2. customA yellow suspension is obtained and after a few minutes
  3. customof stiffing at room temperature
  4. customTriethylamine was removed
  5. customthe crude product was purified by flash chromatography (Prepacked column 10 g, cyclohexane/AcOEt: from 60/40 to 50/50 as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-d043ff7e57074aaaa13aec60c4ecf594
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674106B2

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