HCID 86649678, compound → ethyl 5-trimethylsilyl-1H-indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

0.62 g (0.59 mmol) of the dirhodium(II) heptafluorobutyrate dimer complex is added to a solution of 1.7 g (5.90 mmol) of ethyl 2-azido-3-(3-trimethylsilylphenyl)propenoate prepared according to the procedure described in stage 3.3, in 25 ml of dry toluene, maintained under an inert atmosphere. The reaction mixture is stirred for 7 h at 40° C. A second portion of 0.62 g (0.59 mmol) of the dirhodium(II) heptafluorobutyrate dimer complex is added to the reaction mixture while maintaining the stirring and the heating at 40° C. for a further 1 h. After a return to ambient temperature, the reaction mixture is filtered over silica gel, elution being carried out with toluene. The filtrate is subsequently concentrated under reduced pressure. The greenish solid obtained is triturated several times in a minimum amount of heptane, until a white powder is obtained. The latter is dried under reduced pressure to give 0.87 g of the expected ethyl 5-trimethylsilyl-1H-indole-2-carboxylate in the form of a white powder.

Provenance & Evidence