反应 #66280
ord-a83da1c9318343b2a3473e53415fa069
反应方程式
反应物
试剂
反应条件
后处理
- 1其他was bubbled with N2 for 10 min
- 2其他The resulting mixture was bubbled with N2 for 10 min
- 3温度The reaction mixture was cooled to room temperature
- 4浓缩concentrated under reduced pressure
- 5其他to give the crude material that
- 6过滤The mixture was filtered through GF/F
- 7过滤filter
- 8其他The aqueous layer was separated
- 9萃取extracted with EtOAc (10 mL)
- 10洗涤The combined organic layers were washed with brine (10 mL)
- 11干燥dried over MgSO4
- 12过滤filtered
- 13浓缩concentrated under reduced pressure
- 14其他to give the crude product that
- 15其他was purified by silica gel flash column chromatography (CH2Cl2 to 2% MeOH in CH2Cl2)
实验过程
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.