1-Chloro-4-(chloromethyl)benzene → ethyl 1-(4-chlorobenzyl)-7-methyl-1H-indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

ethyl 7-methyl-1H-indole-2-carboxylate (500 mg, 2.46 mmol) was dissolved in DMF (20 mL) and granular potassium carbonate (425 mg, 3.08 mmol) and p-chlorobenzylchloride (0.39 mL, 3.08 mmol) were added The mixture was stirred for 3 d at 60° C., after which time the incomplete reaction was terminated by dilution with ethyl acetate and subsequent washing with brine (3×). The organic phase was dried over magnesium sulfate, concentrated, and purified vial silica gel flash chromatography (80 g silica, 40% EtOAc/hexanes.) The title compound was obtained as white crystals. (Yield: 390 mg, 1.19 mmol, 46%) 1H NMR (400 MHz, CDCl3) 7.56, 7.41, 7.32-6.96, 6.78, 6.08, 4.31-4.25, 2.54, 1.34

Provenance & Evidence