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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 594022Erstellt: 24. Oktober 2026

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

https://huagongshe.com/de/reaction/594022

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt1,2-DichloroethaneHCID 11—
EduktHOAtHCID 181649—
Edukt4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 16086089—
Edukt2-(2-Cyanopropan-2-yl)isonicotinic acidHCID 57929703—
LösungsmittelWaterHCID 962—
LösungsmittelDimethylformamideHCID 6228—
Produkt2-(2-cyanopropan-2-yl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isonicotinamideHCID 9040904797%

Reaktionsschritte

EDC (1.3 equiv.) was added to a solution of 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.0 equiv.), 2-(2-cyanopropan-2-yl)isonicotinic acid (1.2 equiv.), HOAt (1.3 equiv.) in DMF (0.19 M). The mixture was stirred at ambient temperature 3 hrs. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed sequentially with 1M aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered, and concentrated to yield 2-(2-cyanopropan-2-yl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isonicotinamide in 97% yield. LCMS (m/z) (M+H)=406.2, Rt=1.10 min.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09242969B2
Quelldatensatzuspto-grants-2016_01
ORD IDord-b9e8313eba164bfebc59349c15248445
Quellennotizuspto-grants-2016_01