Dimethyl Sulfoxide → HCID 68153707, compound

HRID 402333Notes

Reaction equation

HRID 402333 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 68153707HCID 68153707, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-87cc4ce7d139499d83fb9c970dcfd567
Source dataset
uspto-grants-2014_06
Patent number
US08742112B2

Reaction notes

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