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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 252617Generated: October 26, 2026

N-Methyl dicyclohexylamine → 1-{(2E)-3-[4-chloro-3-(trifluoromethyl)phenyl]prop-2-en-1-yl}-1H-indole-2,3-dione

https://huagongshe.com/reaction/252617

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN-Methyl dicyclohexylamineHCID 24210—
Reactant4-Bromo-2-chloro-alpha,alpha,alpha-trifluorotolueneHCID 67959—
Reactant1-AllylisatinHCID 1713563—
CatalystHCID 178418851HCID 178418851—
SolventTolueneHCID 1140—
Product1-{(2E)-3-[4-chloro-3-(trifluoromethyl)phenyl]prop-2-en-1-yl}-1H-indole-2,3-dioneHCID 25006661—

Reaction Conditions

Temperature80 °C

Reaction Steps

Six separate oven-dried sealed tubes were charged with 1-allyl-1H-indole-2,3-dione (0.100 g, 0.534 mmol), Pd(P(t-Bu)3)2 (0.0082 g, 0.016 mmol), 4-bromo-1-chloro-2-(trifluoro-methyl)benzene (0.139 g, 0.536 mmol), dry toluene (1 mL), and N-cyclohexyl-N-methyl-cyclohexanamine (0.12 mL, 0.57 mmol) under an atmosphere of N2. The tubes were heated for 16 h at 80° C. in an oil bath, and then the reactions were cooled and concentrated in vacuo. The crude material was used in the subsequent step.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07868181B2
Source datasetuspto-grants-2011_01
ORD IDord-c379774113094b519c0163d5660df5b2
Source noteuspto-grants-2011_01