Pyridine → HCID 58244310, compound

HRID 389092Notes

Reaction equation

HRID 389092 reaction equation
[Cl:1][C:2]1[CH:27]=[N:26][CH:25]=[CH:24][C:3]=1[C:4]([NH:6][NH:7][C:8](=O)[C:9]([CH3:22])([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)[CH3:10])=[O:5].N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:27]=[N:26][CH:25]=[CH:24][C:3]=1[C:4]1[O:5][C:8]([C:9]([CH3:22])([O:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=2)[CH3:10])=[N:7][N:6]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 67024519HCID 67024519, compound

Product 1

HCID 58244310HCID 58244310, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-10 °C

Procedure

3-chloro-N′-{2-methyl-2-[4-(trifluoromethyl)phenoxy]propanoyl}isonicotinohydrazide (282 mg) was dissolved in dichloromethane (5 ml) and pyridine (130 μl) was added thereto. The reaction solution was cooled to −10° C., trifluoromethanesulfonic anhydride (230 μl) was added thereto, followed by standing to warm to room temperature and then stirring overnight. The reaction solution was diluted with saturated aqueous sodium bicarbonate, the organic layer was separated and the aqueous layer was extracted with chloroform. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain 3-chloro-4-(5-{1-methyl-1-[4-(trifluoromethyl)phenoxy]ethyl}-1,3,4-oxadiazol-2-yl)pyridine (231 mg) as a light yellow solid.

Workup

  1. temperatureto warm to room temperature
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with chloroform
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-46b911ee9ba442f59fdeee9d79a863f8
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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