Water → HCID 67487618, Verbindung

HRID 1523605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1523605
[CH3:1][C:2]1[C:3](=[S:8])[NH:4][CH:5]=[CH:6][CH:7]=1.Br[C:10]1[CH:11]=[C:12]([O:18][C:19]2[C:20]([CH3:25])=[N:21][CH:22]=[CH:23][CH:24]=2)[C:13]([C:16]#[N:17])=[N:14][CH:15]=1.[H-].[Na+].O>CN(C=O)C>[CH3:1][C:2]1[C:3]([S:8][C:10]2[CH:11]=[C:12]([O:18][C:19]3[C:20]([CH3:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[C:13]([C:16]#[N:17])=[N:14][CH:15]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 53714503-Methyl-2(1H)-pyridinethioneHCID 67485726HCID 67485726, Verbindung

Produkt 1

HCID 67487618HCID 67487618, VerbindungAusbeute 60,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Methylpyridine-2(1H)-thione (0.906 g, 7.24 mmol) and 5-bromo-3-(2-methylpyridin-3-yloxy)picolinonitrile (2.00 g, 6.89 mmol) were dissolved in DMF (12 mL) and the mixture was cooled to 0° C. Sodium hydride (95%; 0.183 g, 7.24 mmol) was slowly added and the reaction was warmed to ambient temperature and stirred overnight. The reaction mixture was poured into water (100 mL), stirred for 30 minutes, then filtered to afford a solid which was purified over silica gel (2:3 hexanes:ethyl acetate). Concentration of the second UV active fraction to elute afforded 5-(3-methylpyridin-2-ylthio)-3-(2-methylpyridin-3-yloxy)picolinonitrile (1.40 g, 4.19 mmol, 60.7% yield) as a pale yellow/off white powder/crystals.

Aufarbeitung

  1. temperaturethe reaction was warmed to ambient temperature
  2. stirringstirred for 30 minutes
  3. filtrationfiltered
  4. customto afford a solid which
  5. customwas purified over silica gel (2:3 hexanes:ethyl acetate)
  6. washConcentration of the second UV active fraction to elute

Quellen und Nachweise

ORD-Eintrag
ord-5c1db53681604786bd1a55fcc74b9070
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079890B2

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