Pyridine → HCID 86644433, compound

HRID 2404509Notes

Reaction equation

HRID 2404509 reaction equation
[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([S:16][CH2:17][C:18]([F:21])([F:20])[F:19])[C:13]([CH3:22])=[CH:12][C:11]=2[F:23])[N:8]=[C:7]([OH:24])[CH:6]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[F:39][C:40]([I+]C1C=CC=CC=1)([F:48])[C:41]([F:47])([F:46])[C:42]([F:45])([F:44])[F:43]>ClCCl>[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([S:16][CH2:17][C:18]([F:19])([F:20])[F:21])[C:13]([CH3:22])=[CH:12][C:11]=2[F:23])[N:8]=[C:7]([O:24][C:40]([F:48])([F:39])[C:41]([F:47])([F:46])[C:42]([F:45])([F:44])[F:43])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2760327(Heptafluoropropyl)(phenyl)iodanium trifluoromethanesulfonateHCID 178474353HCID 178474353, compound

Product 1

HCID 86644433HCID 86644433, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.1 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-hydroxypyrazole was dissolved in 60 mL of dichloromethane, and 0.51 g of pyridine was added. To the obtained solution, 3.0 g of (perfluoro-n-propyl)phenyliodonium trifluoromethanesulfonate was slowly added, followed by stirring at room temperature for 1 hour. The solvent was distilled off under reduced pressure, a saturated salt solution was added, extraction with ethyl acetate was carried out, the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4) to obtain 0.10 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(1,1,2,2,3,3,3-heptafluoropropoxy)pyrazole.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additiona saturated salt solution was added
  3. extractionextraction with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-a20ff72843154df6814b04bed4d6eaad
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

Loading…