تفاعل #66280
ord-a83da1c9318343b2a3473e53415fa069
معادلة التفاعل
المتفاعلات
الكواشف
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المعالجة
- 1أخرىwas bubbled with N2 for 10 min
- 2أخرىThe resulting mixture was bubbled with N2 for 10 min
- 3درجة الحرارةThe reaction mixture was cooled to room temperature
- 4تركيزconcentrated under reduced pressure
- 5أخرىto give the crude material that
- 6ترشيحThe mixture was filtered through GF/F
- 7ترشيحfilter
- 8أخرىThe aqueous layer was separated
- 9استخلاصextracted with EtOAc (10 mL)
- 10غسيلThe combined organic layers were washed with brine (10 mL)
- 11تجفيفdried over MgSO4
- 12ترشيحfiltered
- 13تركيزconcentrated under reduced pressure
- 14أخرىto give the crude product that
- 15أخرىwas purified by silica gel flash column chromatography (CH2Cl2 to 2% MeOH in CH2Cl2)
الإجراء التجريبي
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.