Reacción #68376

Ecuación de reacción

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

Disolventes

Et2O

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe ether layer was separated
2. 2
   Lavadowashed with brine
3. 3
   Secadodried over MgSO4
4. 4
   Filtraciónfiltered into a flask
5. 5
   workup.ADDITIONcontaining
6. 6
   Temperaturacooled to room temperature
7. 7
   Otroquenched with H2O
8. 8
   Extracciónextracted with EtOAc (×2)
9. 9
   LavadoThe combined organic layer was washed with brine
10. 10
    Secadodried over Na2SO4
11. 11
    Concentraciónconcentrated in vacuo
12. 12
    OtroThe residue was purified
13. 13
    Lavadoby washing with H2O (×3) and filtration

Procedimiento

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.

Fuente