반응 #68376

반응 방정식

2-Bromomethylpyridine

HBr

NaOH

methyl3-formyl-6-methoxy-1H-indole-2-carboxylate

Compound 90

methyl3-formyl-6-methoxy-1H-indole-2-carboxylate

K2CO3

→

title compound

Methyl 3-Formyl-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate

용매

Et2O

DMF

반응 조건

후처리

1. 1
   기타The ether layer was separated
2. 2
   세척washed with brine
3. 3
   건조dried over MgSO4
4. 4
   여과filtered into a flask
5. 5
   workup.ADDITIONcontaining
6. 6
   온도cooled to room temperature
7. 7
   기타quenched with H2O
8. 8
   추출extracted with EtOAc (×2)
9. 9
   세척The combined organic layer was washed with brine
10. 10
    건조dried over Na2SO4
11. 11
    농축concentrated in vacuo
12. 12
    기타The residue was purified
13. 13
    세척by washing with H2O (×3) and filtration

실험 절차

General Procedure J. 2-Bromomethylpyridine.HBr salt (7.0 g, 27.7 mmol) was treated with NaOH (4M, 6.9 ml, 27.6 mmol) in Et2O (20 ml). The ether layer was separated, washed with brine, and dried over MgSO4, filtered into a flask containing a suspension of methyl3-formyl-6-methoxy-1H-indole-2-carboxylate (Compound 90, 1.29 g, 5.54 mmol) and K2CO3 (2.3 g, 16.6 mmol) in DMF (25 ml). The reaction was stirred at 60° C. for 3 h, cooled to room temperature, quenched with H2O and extracted with EtOAc (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by washing with H2O (×3) and filtration to yield the title compound as a golden brown solid.

출처