تفاعل #1483069

معادلة التفاعل

1H-indole-6-carboxylic acid methyl ester

4-methoxybenzyl bromide

sodium hydride

→

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

المردود 54.2%

المذيبات

water

ethyl acetate

DMF

ظروف التفاعل

المعالجة

1. 1
   غسيلthe organic layer was washed again with dilute NaHCO3 (25 mL)
2. 2
   تجفيفThe organic layer was dried over Na2SO4
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated

الإجراء التجريبي

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).

المصدر