Potassium Carbonate → ethyl 5-trimethylsilyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylate

Participants

Reaction Steps

0.32 g (1.68 mmol) of 3-fluorobenzyl bromide and 100 mg (0.31 mmol) of tetrabutyl-ammonium bromide are added, slowly at ambient temperature, to a suspension of 0.4 g (1.53 mmol) of ethyl 5-trimethylsilyl-1H-indole-2-carboxylate, obtained according to the protocol described in stage 3.4, and of 0.64 g (4.59 mmol) of potassium carbonate in 15 ml of dry acetonitrile, maintained under an inert atmosphere. The reaction mixture is stirred at reflux for 2 h. After this period of time, the cooled suspension is filtered through a frit and rinsed with acetonitrile. The reaction crude obtained after evaporation of the filtrate under reduced pressure is purified by flash chromatography on a silica gel column, elution being carried out with a gradient of 5 to 15% of ether in heptane. 0.5 g of the expected ethyl 5-trimethylsilyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylate is thus isolated.

Provenance & Evidence