Réaction #1483067

Équation de réaction

1H-indole-6-carboxylic acid methyl ester

4-difluoromethoxy-benzyl bromide

sodium hydride

→

1-(4-difluoromethoxy-phenylmethyl)-1H-indole-6-carboxylic acid methyl ester

Rendement 21.1%

Solvants

water

ethyl acetate

DMF

Conditions de réaction

Traitement

1. 1
   Lavagethe organic layer was washed again with dilute NaHCO3 (25 mL)
2. 2
   SéchageThe organic layer was dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated

Mode opératoire

To a solution of commercially available 1H-indole-6-carboxylic acid methyl ester (0.35 g, 2.0 mmol) and 4-difluoromethoxy-benzyl bromide (0.52 g, 2.2 mmol) in DMF (2 mL) was added sodium hydride (92 mg, 2.3 mmol). After stirring at room temperature for 3.5 hr, the solution was diluted with water (25 mL) and ethyl acetate (75 mL), the organic layer was washed again with dilute NaHCO3 (25 mL) and then brine (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The remaining residue was subjected to flash chromatography (ethyl acetate/hexane. 1:5) to provide 1-(4-difluoromethoxy-phenylmethyl)-1H-indole-6-carboxylic acid methyl ester as a colorless oil (0.14 g, 21% yield).

Source