تفاعل #69852

معادلة التفاعل

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

المردود 72.6%

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

المردود 72.6%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىwas placed in a microwave tube
2. 2
   أخرىflushed with argon
3. 3
   أخرىThe tube was sealed
4. 4
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
5. 5
   غسيلwashed with water and brine
6. 6
   تجفيفdried over anhydrous sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىThe resulting brown oil was purified by flash chromatography (EtOAc/heptane 3:1)

الإجراء التجريبي

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].

المصدر