반응 #634657

반응 방정식

hydrogen

NaH

1-[2-(1H-indol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

cesium carbonate

→

2

수율 35.9%

2,2-Dimethyl-1-[2-(2-pyrrolidin-1-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

수율 35.9%

용매

toluene acetone

acetonitrile

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGwas stirred at 130° C. under microwave irradiation for two hours
3. 3
   온도before being cooled to RT
4. 4
   기타The reaction mixture was partitioned between EtOAc and saturated aqueous ammonium chloride
5. 5
   추출the aqueous layer was back extracted twice with EtOAc
6. 6
   건조Combined organic layers were dried over Na2SO4
7. 7
   여과filtered
8. 8
   기타evaporated
9. 9
   기타The residue was purified by SiO2 chromatography (hexanes/EtOAc 0-20% EtOAc)

실험 절차

Step 2—A mixture of 1-[2-(1H-indol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.2 g, 0.446 mmol), 1 (0.23 g, 0.892 mmol), and cesium carbonate (0.29 g, 0.892 mmol) in 4 mL of acetonitrile was stirred at 80° C. overnight. TLC (hexanes/EtOAc 7/3) showed little conversion, so NaH 60% dispersion in oil (0.067 g, 1.672 mmol) was added and the after hydrogen evolution had stopped the reaction mixture was stirred at 130° C. under microwave irradiation for two hours before being cooled to RT. The reaction mixture was partitioned between EtOAc and saturated aqueous ammonium chloride, the aqueous layer was back extracted twice with EtOAc. Combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by SiO2 chromatography (hexanes/EtOAc 0-20% EtOAc) and then a second time (toluene/acetone 0-10% acetone) to give 0.028 g of 2 (10% yield)

출처