Pyridine → HCID 86644500, compound

HRID 2404562Notes

Reaction equation

HRID 2404562 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:54])[C:41]([F:53])([F:52])[C:42]([F:51])([F:50])[C:43]([F:49])([F:48])[C:44]([F:47])([F:46])[F:45]>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:54])([F:39])[C:41]([F:52])([F:53])[C:42]([F:50])([F:51])[C:43]([F:48])([F:49])[C:44]([F:47])([F:46])[F:45])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 86644501HCID 86644501, compoundHCID 178474353HCID 178474353, compound2×

Product 1

HCID 86644500HCID 86644500, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-hydroxypyrazole was dissolved in 30 mL of dichloromethane, 2.18 g of pyridine was added, and the above prepared crude (perfluoropentyl)phenyliodonium trifluoromethanesulfonate was added at room temperature until 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-hydroxypyrazole disappeared (disappearance was confirmed by thin layer chromatography). Then, 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=1:3) to obtain 0.64 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(1,1,2,2,3,3,4,4,5,5,5-undecafluoropentyloxy)pyrazole.

Workup

  1. distillationThen, the 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=1:3)

Sources & evidence

ORD record
ord-7753ddd5aa444ede947e45f6aa05123e
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

Loading…