反応 #1483071

反応方程式

1H-indole-6-carboxylic acid methyl ester

3-nitrobenzyl bromide

K2CO3

→

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

収率 76.0%

溶媒

DMF

ethyl acetate

反応条件

後処理

1. 1
   洗浄washed with water (3×50 ml)
2. 2
   乾燥The organic layer was dried (MgSO4)
3. 3
   ろ過filtered
4. 4
   濃縮concentrated
5. 5
   その他The remaining residue was recrystallized with ethyl acetate/hexane

実験手順

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).

出典