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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 594024Generated: October 25, 2026

1,2-Dichloroethane → N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-(trifluoromethyl)isonicotinamide

https://huagongshe.com/reaction/594024

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DichloroethaneHCID 11—
Reactant3-(Trifluoromethyl)benzoic acidHCID 9963—
ReactantHOAtHCID 181649—
Reactant4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 16086089—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
ProductN-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-(trifluoromethyl)isonicotinamideHCID 9040853491%

Reaction Steps

To a mixture of 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.0 equiv.) and 3-(trifluoromethyl)benzoic acid (1.1 equiv.) in DMF (0.27 M) was added HOAt (1.3 equiv.) and EDC (1.3 equiv.) After 3 h the reaction mixture was diluted with water and then extracted with EtOAc. The organic phase was washed sequentially with 1 M aqueous sodium hydroxide and brine and was then dried over sodium sulfate. The solution was concentrated and dried under vacuo to give N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-(trifluoromethyl)isonicotinamide in 91% yield. LCMS (m/z) (M+H)=407.1, Rt=1.13 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09242969B2
Source datasetuspto-grants-2016_01
ORD IDord-009e13668b99438fbb81b0af0d1aed39
Source noteuspto-grants-2016_01