反应 #90030

ord-b9d0a98fe4834385af7afb06cd46afe8

溶剂

反应条件

温度
80°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The mixture was subjected to reduced pressure under ultrasonication treatment
  2. 2
    其他by flushing with nitrogen gas
  3. 3
    其他degassed
  4. 4
    温度the mixture was cooled to room temperature
  5. 5
    workup.ADDITIONadded with water (250 ml)
  6. 6
    workup.STIRRINGfurther stirred for 30 min
  7. 7
    过滤The precipitates were filtered
  8. 8
    洗涤washed with water (50 ml)
  9. 9
    洗涤They were further washed with CH3CN (50 ml)

实验过程

To trifluoro-methanesulfonic acid 3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yl ester (Compound B1, 7.80 g, 18.0 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (6.11 g, 19.8 mmol, 1.1 eq.), Pd(PPh3)2Cl2 (630 mg, 0.898 mmol, 0.05 eq.), and sodium carbonate (5.71 g, 53.9 mmol, 3.0 eq.), DME (125 ml) and water (25 ml) were added. The mixture was subjected to reduced pressure under ultrasonication treatment, followed by flushing with nitrogen gas. This procedure was repeated five times and then degassed. After further stirring at 80° C. for 2 hr under nitrogen atmosphere, the mixture was cooled to room temperature, added with water (250 ml), and further stirred for 30 min. The precipitates were filtered and washed with water (50 ml). They were further washed with CH3CN (50 ml) to obtain the target compound as a crude product (gray powder, 7.54 g, 90%).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US09440922B2uspto-grants-2016_09