Pyridine → HCID 11612909, compound

HRID 2243785Notes

Reaction equation

HRID 2243785 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([Cl:18])[C:9]=1[N:19]1[C:23]([N:24]([CH2:26][CH2:27]O)[CH3:25])=[C:22]([S:29]([C:32]([F:35])([F:34])[F:33])(=[O:31])=[O:30])[C:21]([C:36]#[N:37])=[N:20]1>ClCCl.[O-2].[Cr+6].[O-2].[O-2]>[Cl:18][C:10]1[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=[C:8]([Cl:7])[C:9]=1[N:19]1[C:23]([N:24]([CH3:25])[CH:26]=[CH2:27])=[C:22]([S:29]([C:32]([F:35])([F:33])[F:34])(=[O:30])=[O:31])[C:21]([C:36]#[N:37])=[N:20]1

Participants

5

Reactant 2

HCID 1049PyridineHCID 86611439HCID 86611439, compound

Product 1

HCID 11612909HCID 11612909, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of pyridine (0.186 g, 0.23 mmol) in dichloromethane (10 mL) was slowly added chromium (VI) oxide (0.119 g, 0.12 mmol) at room temperature under nitrogen. The resulting mixture was stirred at room temperature for 15 minutes before 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-hydroxy-ethyl)(methyl)amino]-4-[(trifluoromethyl)sulfonyl]-1H-pyrazole-3-carbonitrile (0.200 g, 0.4 mmol) was introduced. The reaction mixture was allowed to stirr at room temperature for two additional hours. It was then concentrated to dryness and then diluted with diethyl ether. The mixture was then filtered through silica gel and then concentrated to afford a pale oil (0.04 g, 0.1 mmol). 19F NMR: −64.37, −80.74.

Workup

  1. customat room temperature
  2. additionwas introduced
  3. customto stirr at room temperature for two additional hours
  4. concentrationIt was then concentrated to dryness
  5. additiondiluted with diethyl ether
  6. filtrationThe mixture was then filtered through silica gel
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-518890e12b134ceb96300bb776220202
Source dataset
uspto-grants-2010_03
Patent number
US07678384B2

Reaction notes

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