反応 #66280
ord-a83da1c9318343b2a3473e53415fa069
反応方程式
反応物
試薬
反応条件
後処理
- 1その他was bubbled with N2 for 10 min
- 2その他The resulting mixture was bubbled with N2 for 10 min
- 3温度The reaction mixture was cooled to room temperature
- 4濃縮concentrated under reduced pressure
- 5その他to give the crude material that
- 6ろ過The mixture was filtered through GF/F
- 7ろ過filter
- 8その他The aqueous layer was separated
- 9抽出extracted with EtOAc (10 mL)
- 10洗浄The combined organic layers were washed with brine (10 mL)
- 11乾燥dried over MgSO4
- 12ろ過filtered
- 13濃縮concentrated under reduced pressure
- 14その他to give the crude product that
- 15その他was purified by silica gel flash column chromatography (CH2Cl2 to 2% MeOH in CH2Cl2)
実験手順
To Na2CO3 (129 mg, 1.214 mmol) in a 50 mL round-bottom flask was added water (3.7 mL) was bubbled with N2 for 10 min. To this mixture was added tert-butyl (1E,4E)-8-bromo-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-ylcarbamate (200 mg, 0.40 mmol) in EtOH (4.9 mL) at room temperature. The resulting mixture was bubbled with N2 for 10 min. Pd(OAc)2 (9.3 mg, 0.040 mmol) and 4,4′-(phenylphosphinidene)bisbenzenesulfonic acid dipotassium hydrate (45 mg, 0.081 mmol) were added. The resulting mixture was warmed to 65° C. with N2 bubbling. To this mixture was added a solution of 4-(dimethylcarbamoyl)phenylboronic acid (97 mg, 0.49 mmol) in EtOH (0.6 mL). The resulting mixture was stirred at 65° C. for 1 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure to give the crude material that was diluted with water (5 mL) and EtOAc (10 mL). The mixture was filtered through GF/F filter. The aqueous layer was separated and extracted with EtOAc (10 mL). The combined organic layers were washed with brine (10 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude product that was purified by silica gel flash column chromatography (CH2Cl2 to 2% MeOH in CH2Cl2) to afford 178 mg (83%) of tert-butyl (1E,4E)-8-(4-(dimethylcarbamoyl)phenyl)-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-ylcarbamate. MS APCI(+) m/z 533 (M+1) detected.