Reaction #1483069

Reaction equation

1H-indole-6-carboxylic acid methyl ester

4-methoxybenzyl bromide

sodium hydride

→

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

Yield 54.2%

Solvents

water

ethyl acetate

DMF

Conditions

Workup

1. 1
   Washthe organic layer was washed again with dilute NaHCO3 (25 mL)
2. 2
   DryingThe organic layer was dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated

Procedure

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).

Source