Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 588281Generated: October 30, 2026

Piperidine → 5-[(Z)-(5-bromo-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

https://huagongshe.com/reaction/588281

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPiperidineHCID 8082—
Reactant5-Bromo-2-oxindoleHCID 611193—
ReactantN-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamideHCID 20761785—
SolventEthanolHCID 702—
Product5-[(Z)-(5-bromo-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-carboxamideHCID 532910471.5%

Reaction Conditions

Temperature80 °C

Reaction Steps

To the solution of 5-bromoindolin-2-one (262 mg, 1.24 mmol) in EtOH (5 ml) was added N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide (298 mg, 1.12 mmol) and piperidine (112 μL, 1.13 mmol). The mixture was stirred at 80° C. for 1 hour. After cooled down to room temperature, the reaction mixture was concentrated, filtrated, and washed with EtOH to give (Z)-5-((5-bromo-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide (368 mg) as orange solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09227962B2
Source datasetuspto-grants-2016_01
ORD IDord-72bcb744cdc447dcaa60f672a7c3f44a
Source noteuspto-grants-2016_01