Реакция #68376

Уравнение реакции

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

Растворители

Et2O

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe ether layer was separated
2. 2
   Промывкаwashed with brine
3. 3
   Сушкаdried over MgSO4
4. 4
   Фильтрацияfiltered into a flask
5. 5
   workup.ADDITIONcontaining
6. 6
   Температураcooled to room temperature
7. 7
   Другоеquenched with H2O
8. 8
   Экстракцияextracted with EtOAc (×2)
9. 9
   ПромывкаThe combined organic layer was washed with brine
10. 10
    Сушкаdried over Na2SO4
11. 11
    Концентрированиеconcentrated in vacuo
12. 12
    ДругоеThe residue was purified
13. 13
    Промывкаby washing with H2O (×3) and filtration

Методика

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.

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