반응 #68385

반응 방정식

MeMgBr

N-(3,4-difluorobenzyl)-2-formyl-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

Compound 105

N-(3,4-difluorobenzyl)-2-formyl-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

MeMgBr

→

title compound

N-(3,4-Difluorobenzyl)-2-(1-hydroxyethyl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

용매

1,2-dimethoxy-ethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred at room temperature for another 2 h
2. 2
   기타was quenched with ice
3. 3
   추출extracted with EtOAc
4. 4
   세척The organic layer was washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   농축concentrated in vacuo
7. 7
   기타The residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes)

실험 절차

To a solution of N-(3,4-difluorobenzyl)-2-formyl-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide (Compound 105, 102 mg, 0.23 mmol) in 1,2-dimethoxy-ethane (15 ml) was added MeMgBr (1.4 M in toluene-THF, 0.5 ml, 0.70 mmol) at 0° C. The reaction was stirred at room temperature for 2 h and more MeMgBr (1.0 ml, 1.4 mmol) was added. The reaction was stirred at room temperature for another 2 h and was quenched with ice, extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes) to yield the title compound.

출처