Reaction #1483071

Reaction equation

1H-indole-6-carboxylic acid methyl ester

3-nitrobenzyl bromide

K2CO3

→

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

Yield 76.0%

Solvents

DMF

ethyl acetate

Conditions

Workup

1. 1
   Washwashed with water (3×50 ml)
2. 2
   DryingThe organic layer was dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   OtherThe remaining residue was recrystallized with ethyl acetate/hexane

Procedure

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).

Source