Réaction #1483079

Équation de réaction

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

Rendement 22.0%

Solvants

ether

Conditions de réaction

Traitement

1. 1
   Températurewere heated
2. 2
   Températureto reflux for 16 hr
3. 3
   Températurethe solution was heated
4. 4
   Températureat reflux an additional 4 hr
5. 5
   Lavagewashed with aq. NH4Cl (50 mL)
6. 6
   SéchageThe organic layer was dried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated

Mode opératoire

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).

Source