Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 502270Generated: November 3, 2026

Dimethylformamide → 1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole

https://huagongshe.com/reaction/502270

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantCesium carbonateHCID 10796—
ReactantBromomethylcyclopropaneHCID 81503—
Reactant6-ethoxy-2-(4-nitro-phenyl)-1H-indoleHCID 59030425—
SolventWaterHCID 962—
Product1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indoleHCID 5903042688%

Reaction Steps

6-Ethoxy-2-(4-nitro-phenyl)-1H-indole (4.5 g, 16 mmol), Cs2CO3 (7.8 g, 24 mmol), DMF (23 mL), and bromomethylcyclopropane (1.8 mL, 18 mmol) were stirred at 80° C. in a sealed tube for 16 hours. The reaction mixture was diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O and brine and then dried and concentrated. Purification by silica gel chromatography (1:1 CH2Cl2/hexane) provided 1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole (4.73 g, 88%) as an orange solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07772271B2
Source datasetuspto-grants-2010_08
ORD IDord-30a61c31ea61401787f5f6a3dc3872f8
Source noteuspto-grants-2010_08