Reacción #77566

Ecuación de reacción

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

Disolventes

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Otrothe organic layer was collected
3. 3
   Extracciónthe aqueous layer was extracted with chloroform
4. 4
   Secadodried over anhydrous sodium sulfate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe residue was purified by column chromatography on silica gel
7. 7
   Otroto yield crude crystals
8. 8
   OtroThe crude crystals were recrystallized from chloroform-hexane

Procedimiento

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%).

Fuente