Reacción #1483079

Ecuación de reacción

4-fluoro-benzyl bromide

1-methyl-1H-indole-5-carboxylic acid methyl ester

4-fluoro-benzyl bromide

dioxane

→

3-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester

Rendimiento 22.0%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawere heated
2. 2
   Temperaturato reflux for 16 hr
3. 3
   Temperaturathe solution was heated
4. 4
   Temperaturaat reflux an additional 4 hr
5. 5
   Lavadowashed with aq. NH4Cl (50 mL)
6. 6
   SecadoThe organic layer was dried over MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

A solution of 1-methyl-1H-indole-5-carboxylic acid methyl ester (0.17 g, 0.9 mmol), prepared using procedures as described in Example 1, Ag2O) (0.22 g, 0.95 mmol), 4-fluoro-benzyl bromide (0.18 g, 0.95 mmol) and dioxane (4 mL) were heated to reflux for 16 hr, then more 4-fluoro-benzyl bromide (90 mg, 0.5 mmol) was added and the solution was heated at reflux an additional 4 hr. After cooling to room temperature, the reaction mixture was diluted with ether (60 mL), washed with aq. NH4Cl (50 mL) and then brine (50 mL). The organic layer was dried over MgSO4, filtered and concentrated. The remaining residue was subjected to flash chromatography (ethyl acetate/hexane, 1:3) to provide 3-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (58 mg, 22% yield).

Fuente