反应 #69852

反应方程式

2-((1-tosyl-1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one

3-bromoquinoline

sodium t-butanolate

2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethylaniline

→

title compound

收率 72.6%

9-(quinolin-3-yl)-2-((1-tosyl-1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one

收率 72.6%

溶剂

dioxane

反应条件

后处理

1. 1
   其他was placed in a microwave tube
2. 2
   其他flushed with argon
3. 3
   其他The tube was sealed
4. 4
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
5. 5
   洗涤washed with water and brine
6. 6
   干燥dried over anhydrous sodium sulfate
7. 7
   过滤filtered
8. 8
   浓缩concentrated under reduced pressure
9. 9
   其他The resulting brown oil was purified by flash chromatography (EtOAc/heptane 3:1)

实验过程

The mixture of 2-((1-tosyl-1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one (100 mg, 0.15 mmol, contains 1.7 moleq TFA), 3-bromoquinoline (49 mg, 0.23 mmol), Pd2dba3 (7 mg, 7.7 μmol), sodium t-butanolate (45 mg, 0.46 mmol), 2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethylaniline (DavePhos, 6.1 mg, 0.015 mmol) and dry dioxane (2 mL) was placed in a microwave tube and flushed with argon. The tube was sealed and the suspension was heated at 100° C. for 1 h under microwave conditions. The reaction mixture was diluted with ethyl acetate and washed with water and brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting brown oil was purified by flash chromatography (EtOAc/heptane 3:1) to yield the title compound (63 mg, 68%). [LCMS RtA=1.31 min, [M+H]+=579.2].

来源