Reacción #1483071

Ecuación de reacción

1H-indole-6-carboxylic acid methyl ester

3-nitrobenzyl bromide

K2CO3

→

1-(3-nitrobenzyl)-1H-indole-6-carboxylic acid methyl ester

Rendimiento 76.0%

Disolventes

DMF

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water (3×50 ml)
2. 2
   SecadoThe organic layer was dried (MgSO4)
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe remaining residue was recrystallized with ethyl acetate/hexane

Procedimiento

To a solution of 1H-indole-6-carboxylic acid methyl ester (1.0 g, 5.7 mmol) and 3-nitrobenzyl bromide (1.48 g, 6.8 mmol) in DMF (15 mL) was added K2CO3 (1.6 g, 11.4 mmol). After stirring at room temperature for 16 hr, the solution was diluted with ethyl acetate (100 ml) and washed with water (3×50 ml). The organic layer was dried (MgSO4), filtered and concentrated. The remaining residue was recrystallized with ethyl acetate/hexane to provide 1.34 g (76% yield) of 1-(3-nitrobenzyl)-1H-indole-6-carboxylic acid methyl ester as light orange crystals. 1H NMR (300 MHz, DMSO) δ 8.13 (m, 2H), 8.03 (s, 1H), 7.81 (d, 1H, J=3.0 Hz), 7.67-7.54 (m, 4H, J=9.0 Hz), 6.65 (d, 1H, J=3.0 Hz), 5.73 (s, 2H), 3.81 (s, 3H).

Fuente