Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 582268Generated: October 31, 2026

Diglyme → 1-[2,6-Dichloro4-(4-trifluoromethylphenyl)phenyl]-3-cyano-4-trifluoromethylthio-5-aminopyrazole

https://huagongshe.com/reaction/582268

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiglymeHCID 8150—
ReactantPotassium CarbonateHCID 11430—
Reactant4-(Trifluoromethyl)phenylboronic acidHCID 2734389—
Reactant5-Amino-3-cyano-1-(2,6-dichloro-4-bromophenyl)4-trifluoromethylthiopyrazoleHCID 15430816—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
Product1-[2,6-Dichloro4-(4-trifluoromethylphenyl)phenyl]-3-cyano-4-trifluoromethylthio-5-aminopyrazoleHCID 1543081756.5%

Reaction Conditions

Temperature20 °C

Reaction Steps

A mixture of 6 g of 5-amino-3-cyano-1-(2,6-dichloro-4-bromophenyl)4-trifluoromethylthiopyrazole (prepared according to procedures reported in U.S. Pat. No. 5,232,940), 4-trifluoromethylphenylboronic acid (5.3 g), K2CO3 (5.8 g), tris(dibenzylidene acetone)dipalladium (0.6 g) and diglyme was heated at 130° C. for 25 hours. After cooling to 20° C., the mixture was poured into water and extracted with diethyl ether. The ether solutions were combined, dried, filtered and the filtrate concentrated and purified by chromatography. The desired product as a solid (3.9 g, mp 181-184° C.) was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05922884
Source datasetuspto-grants-1999_07
ORD IDord-62b680b8926942aba4364ccbd3fe33fc
Source noteuspto-grants-1999_07