Reacción #1483069

Ecuación de reacción

1H-indole-6-carboxylic acid methyl ester

4-methoxybenzyl bromide

sodium hydride

→

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

Rendimiento 54.2%

Disolventes

water

ethyl acetate

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothe organic layer was washed again with dilute NaHCO3 (25 mL)
2. 2
   SecadoThe organic layer was dried over Na2SO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated

Procedimiento

To a solution of commercially available 1H-indole-6-carboxylic acid methyl ester (0.35 g, 2.0 mmol) and 4-methoxybenzyl bromide (0.32 mL, 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-methoxy-phenylmethyl)-1H-indole-6-carboxylic acid methyl ester as a white solid (0.32 g, 54% yield). 1H NMR (400 MHz, DMSO) δ 8.10 (s, 1H), 7.73 (d, 1H, J=3.4 Hz), 7.64 (m, 2H), 7.14 (d, 2H, J=9.0 Hz), 6.88 (d, 2H, J=9.0 Hz), 6.58 (d, 1H, J=3.4 Hz), 5.45 (s, 2H), 3.83 (s, 3H), 3.70 (s, 3H).

Fuente