تفاعل #1483071

معادلة التفاعل

1H-indole-6-carboxylic acid methyl ester

3-nitrobenzyl bromide

K2CO3

→

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

المردود 76.0%

المذيبات

DMF

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with water (3×50 ml)
2. 2
   تجفيفThe organic layer was dried (MgSO4)
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   أخرىThe remaining residue was recrystallized with ethyl acetate/hexane

الإجراء التجريبي

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).

المصدر