反応 #77566

反応方程式

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

溶媒

反応条件

後処理

1. 1
   温度After cooling
2. 2
   その他the organic layer was collected
3. 3
   抽出the aqueous layer was extracted with chloroform
4. 4
   乾燥dried over anhydrous sodium sulfate
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他The residue was purified by column chromatography on silica gel
7. 7
   その他to yield crude crystals
8. 8
   その他The crude crystals were recrystallized from chloroform-hexane

実験手順

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%).

出典