Potassium Carbonate → HCID 90405969, Verbindung

HRID 2175933

Reaktionsgleichung

Reaktionsgleichung von HRID 2175933
Br[C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[N:17]1[NH:18][N:19]=[CH:20][CH:21]=1>CN(C=O)C>[CH3:8][C:6]1[CH:7]=[C:2]([N:18]2[N:19]=[CH:20][CH:21]=[N:17]2)[C:3]([C:9]#[N:10])=[N:4][CH:5]=1.[CH3:8][C:6]1[CH:7]=[C:2]([N:17]2[CH:21]=[CH:20][N:19]=[N:18]2)[C:3]([C:9]#[N:10])=[N:4][CH:5]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 675161H-1,2,3-TriazoleHCID 225912183-Bromo-5-methylpyridine-2-carbonitrile

Produkt 2

HCID 904052945-methyl-3-(1H-1,2,3-triazol-1-yl)picolinonitrileAusbeute 27 %HCID 90405969HCID 90405969, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 3-bromo-5-methylpicolinonitrile (1.5 g, 7.6 mmol) in DMF (19 mL) was added K2CO3 (1.2 g, 8.4 mmol) and 2H-1,2,3-triazole (440 μL, 7.6 mmol). The mixture was heated to 100° C. for 16 h, cooled to rt and extracted with EtOAc (2×). The combined organics were dried (Na2SO4) and concentrated. Purification via silica gel chromatography (5-60% EtOAc in hexanes) gave the title compound (490 mg, 35%) 1H NMR (500 MHz, CDCl3) 8.58-8.53 (m, 1H), 8.29-8.24 (m, 1H), 7.98 (s, 2H), 2.54 (s, 3H) and 5-methyl-3-(1H-1,2,3-triazol-1-yl)picolinonitrile (387 mg, 27%).

Aufarbeitung

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc (2×)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification via silica gel chromatography (5-60% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2c1069577896459289365f0e42c32386
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062078B2

Verknüpfte Notizen

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