Dimethyl Sulfoxide → HCID 68153707, Verbindung

HRID 402333

Reaktionsgleichung

Reaktionsgleichung von HRID 402333
[NH2:1][C:2]1[C:3]([SH:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[F:13][C:14]1[CH:21]=[N:20][CH:19]=[CH:18][C:15]=1[CH:16]=O.CS(C)=O>O>[F:13][C:14]1[CH:21]=[N:20][CH:19]=[CH:18][C:15]=1[C:16]1[S:12][C:3]2[C:2]([N:1]=1)=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][N:4]=2

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 27630033-FluoroisonicotinaldehydeHCID 178507667HCID 178507667, Verbindung

Produkt 1

HCID 68153707HCID 68153707, VerbindungAusbeute 39,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of 0.90 g of 3-amino-5-(trifluoromethyl)-pyridine-2-thiol, 0.58 g of 3-fluoroisonicotinaldehyde and 5 ml of DMSO was stirred at 170° C. for 2 hours. The reaction mixture was cooled down to room temperature, then, to the reaction mixture was added water, and the resultant mixture was extracted with ethyl acetate twice. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, to obtain 0.55 g of 2-(3-fluoropyridin-4-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter, referred to as the present compound 9).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionthe resultant mixture was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with water and saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-87cc4ce7d139499d83fb9c970dcfd567
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742112B2

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