反応 #1483069

反応方程式

1H-indole-6-carboxylic acid methyl ester

4-methoxybenzyl bromide

sodium hydride

→

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

収率 54.2%

溶媒

water

ethyl acetate

DMF

反応条件

後処理

1. 1
   洗浄the organic layer was washed again with dilute NaHCO3 (25 mL)
2. 2
   乾燥The organic layer was dried over Na2SO4
3. 3
   ろ過filtered
4. 4
   濃縮concentrated

実験手順

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).

出典