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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 58632Generated: October 29, 2026

Sodium Azide → 3-(2-azidoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole

https://huagongshe.com/reaction/58632

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium AzideHCID 33557—
Reactant3-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indoleHCID 66831896—
SolventDimethylformamideHCID 6228—
Product3-(2-azidoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indoleHCID 86663837105.7%

Reaction Conditions

Temperature70 °C

Reaction Steps

A mixture of 3-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole (0.725 g; 1.87 mmol) and sodium azide (0.365 g; 5.62 mmol) in DMF (8 mL) was stirred at 70° C. for 4 hours and concentrated under reduced pressure. The residue was diluted in ethyl acetate, washed with brine, dried and concentrated under reduced pressure to afford 0.690 g (quantitative yield) of the title compound as a brown oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09434722B2
Source datasetuspto-grants-2016_09
ORD IDord-6073c47f3d4440c99df1cb370eb2305f
Source noteuspto-grants-2016_09