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

Temperature

40 °C

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 the preceding step, in 25 mL of dry toluene, maintained under an inert atmosphere, is added 0.62 g (0.59 mmol) of dirhodium (II) heptafluorobutyrate dimer complex. The reaction mixture is stirred for 7 hours at 40° C. A second portion of 0.62 g (0.59 mmol) of dirhodium (II) heptafluorobutyrate dimer complex is added to the reaction mixture while maintaining the stirring and heating at 40° C. for a further 1 hour. After cooling to room temperature, the reaction mixture is filtered through silica gel, eluting with toluene. The filtrate is then concentrated under reduced pressure. The greenish solid obtained is triturated several times in a minimum amount of heptane, until a white powder is obtained. This powder 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.

1. temperaturemaintained under an inert atmosphere
2. temperaturewhile maintaining the stirring and
3. temperatureheating at 40° C. for a further 1 hour
4. temperatureAfter cooling to room temperature
5. filtrationthe reaction mixture is filtered through silica gel
6. washeluting with toluene
7. concentrationThe filtrate is then concentrated under reduced pressure
8. customThe greenish solid obtained
9. customis triturated several times in a minimum amount of heptane
10. customuntil a white powder is obtained
11. customThis powder is dried under reduced pressure

ORD record

ord-ed2427893f40451396d041bd4f301acc

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354425B2