Reaktion #77566

Reaktionsgleichung

potassium carbonate

phenylboronic acid

1,4-bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine

→

title compound

1,4-Bis(5-phenyl-2-pyridyl)hexahydro-1,4-diazepine

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Sonstigethe organic layer was collected
3. 3
   Extraktionthe aqueous layer was extracted with chloroform
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by column chromatography on silica gel
7. 7
   Sonstigeto yield crude crystals
8. 8
   SonstigeThe crude crystals were recrystallized from chloroform-hexane

Vorschrift

Under nitrogen, to a solution of the 1,4-bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine (200 mg, 0.585 mmol) synthesized in Reference Example 1 in ethanol-toluene (2.0 mL-2.0 mL) were added phenylboronic acid (130.0 mg, 1.07 mmol), tetrakis(triphenylphosphine)palladium (56.0 mg, 0.050 mmol) and a 2.0 M aqueous potassium carbonate (0.5 mL, 1.0 mmol), and the resulting mixture was stirred at 80° C. for 3 hours. After cooling, the organic layer was collected and the aqueous layer was extracted with chloroform. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield crude crystals. The crude crystals were recrystallized from chloroform-hexane to yield the title compound as slightly yellow needles (melting point: 221.0-222.0° C.) (61.0 mg, yield: 31%).

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