Dimethylformamide → HCID 90405969, Verbindung

HRID 64197

Reaktionsgleichung

Reaktionsgleichung von HRID 64197
Br[C:2]1[C:3]([C:9](O)=O)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[N:18]1[NH:19][N:20]=[CH:21][CH:22]=1.C[N:24](C=O)C>>[CH3:8][C:6]1[CH:7]=[C:2]([N:19]2[N:20]=[CH:21][CH:22]=[N:18]2)[C:3]([C:9]#[N:24])=[N:4][CH:5]=1.[CH3:8][C:6]1[CH:7]=[C:2]([N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)[C:3]([C:9]#[N:24])=[N:4][CH:5]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 675161H-1,2,3-TriazoleHCID 533955823-Bromo-5-methylpyridine-2-carboxylic acid

Produkt 2

HCID 90405294HCID 90405294, VerbindungAusbeute 27 %HCID 90405969HCID 90405969, VerbindungAusbeute 35 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 3-bromo-5-methylpicolinic acid (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 room temperature 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, Chloroform-d) 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 room temperature
  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-1baf487d47f44e3d87c80186863a189b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447117B2

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