Реакция #1483069

Уравнение реакции

1H-indole-6-carboxylic acid methyl ester

4-methoxybenzyl bromide

sodium hydride

→

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

Выход 54.2%

Растворители

water

ethyl acetate

DMF

Условия реакции

Обработка

1. 1
   Промывкаthe organic layer was washed again with dilute NaHCO3 (25 mL)
2. 2
   СушкаThe organic layer was dried over Na2SO4
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated

Методика

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).

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