反応 #69852

反応方程式

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

収率 72.6%

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

収率 72.6%

溶媒

dioxane

反応条件

後処理

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

実験手順

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].

出典