Triethylamine → Methyl 5-chloro-6-cyano-2-(3-fluorophenyl)nicotinate

HRID 717816Notizen

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:20]([N:22](CC)CC)C.C[Si](C#N)(C)C>C(#N)C>[Cl:1][C:2]1[C:3]([C:20]#[N:22])=[N:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

Methyl 5-chloro-2-(3-fluorophenyl)nicotinate 1-oxide (2.9 g, 10 mmol) was stirred in acetonitrile (30 mL) with triethylamine (2.2 mL, 16 mmol) and trimethylsilyl cyanide (3.4 mL, 26 mmol) was added. The mixture was heated at 70° C. for 1 hour. Evaporation and purification by flash column chromatography using ethyl acetate in hexanes (0-20%) gave the desired compound (2.7 g, 90%). LCMS calculated for C14H9ClFN2O2 (M+H)+: m/z=291.1. found: 290.8.

Aufarbeitung

additionwas added
customEvaporation and purification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-4503de346bc442439c003d275e7187d6
Quelldatensatz: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09193721B2

Notizen zur Reaktion

Wird geladen…