반응 #66280
ord-a83da1c9318343b2a3473e53415fa069
반응 방정식
반응물
시약
반응 조건
후처리
- 1기타was bubbled with N2 for 10 min
- 2기타The resulting mixture was bubbled with N2 for 10 min
- 3온도The reaction mixture was cooled to room temperature
- 4농축concentrated under reduced pressure
- 5기타to give the crude material that
- 6여과The mixture was filtered through GF/F
- 7여과filter
- 8기타The aqueous layer was separated
- 9추출extracted with EtOAc (10 mL)
- 10세척The combined organic layers were washed with brine (10 mL)
- 11건조dried over MgSO4
- 12여과filtered
- 13농축concentrated under reduced pressure
- 14기타to give the crude product that
- 15기타was purified by silica gel flash column chromatography (CH2Cl2 to 2% MeOH in CH2Cl2)
실험 절차
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.