반응 #172230

반응 방정식

5-(3,4,5-Trimethoxy-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one

TMEDA

THF

Benzyl bromide

THF

n-BuLi

→

title compound

수율 38.0%

3,3-dibenzyl-5-(3,4,5-trimethoxy-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one

수율 38.0%

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONaddition
3. 3
   workup.ADDITIONaddition the reaction
4. 4
   workup.STIRRINGwhile stirring overnight
5. 5
   기타The reaction was quenched by the addition of MeOH
6. 6
   기타evaporated
7. 7
   기타partitioned between water and DCM
8. 8
   세척Silica gel chromatography eluting with 0-50% EtOAc

실험 절차

5-(3,4,5-Trimethoxy-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (95 mg, 0.316 mmol) and TMEDA (96 μl, 0.623 mmol) were dissolved in anhydrous THF (4 ml) and cooled to −78° C. n-BuLi (1.6 M in hexanes, 415 μl, 0.664 mmol) was added dropwise. After completed addition stirring was continued for 1 hr at −78° C. Benzyl bromide (41.3 μl, 0.348 mmol) was added dropwise as a 10% solution in anh. THF. After completed addition the reaction was allowed to warm up to room temperature while stirring overnight. The reaction was quenched by the addition of MeOH, evaporated and partitioned between water and DCM. Silica gel chromatography eluting with 0-50% EtOAc:Hexanes yielded the title compound (47 mg, 38%).

출처