Реакция #69852

Уравнение реакции

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

Выход 72.6%

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

Выход 72.6%

Растворители

dioxane

Условия реакции

Обработка

1. 1
   Другоеwas placed in a microwave tube
2. 2
   Другоеflushed with argon
3. 3
   ДругоеThe tube was sealed
4. 4
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
5. 5
   Промывкаwashed with water and brine
6. 6
   Сушкаdried over anhydrous sodium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated under reduced pressure
9. 9
   ДругоеThe resulting brown oil was purified by flash chromatography (EtOAc/heptane 3:1)

Методика

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].

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