Pyridine → HCID 86645105, compound

HRID 658349Notes

Reaction equation

HRID 658349 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4]([C:12]([C:14]2[CH:15]=[N:16][N:17]([CH3:20])[C:18]=2[OH:19])=[O:13])[C:3]1=[O:21].N1C=CC=CC=1.C(Cl)(Cl)Cl.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>O>[CH3:1][N:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][CH:5]=[C:4]([C:12]([C:14]2[CH:15]=[N:16][N:17]([CH3:20])[C:18]=2[O:19][S:38]([C:35]2[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=2)(=[O:40])=[O:39])=[O:13])[C:3]1=[O:21]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 178481841HCID 178481841, compound

Product 1

HCID 86645105HCID 86645105, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of 4-[1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridine-3-carbonyl]-5-hydroxy-1-methyl-1H-pyrazole (0.25 g, 0.80 mmol), pyridine (0.13 g, 1.6 mmol) and chloroform (5 mL), p-toluenesulfonyl chloride (0.23 g, 1.2 mmol) was added little at a time. After the stirring for a day at room temperature, the reaction mixture was poured into water and extracted with chloroform. The organic layer was washed with water, and dried over anhydrous magnesium sulfate. After separating the inorganic substance by filtration, the solvent was distilled off under reduced pressure, and thus obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/1.5), to obtain 0.33 g of a subject compound (yield: 92%).

Workup

  1. waitAfter the stirring for a day at room temperature
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter separating the inorganic substance
  6. filtrationby filtration
  7. distillationthe solvent was distilled off under reduced pressure, and thus obtained residue
  8. customwas purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/1.5)

Sources & evidence

ORD record
ord-07fb4bc23c9949a997f91e99b19aeec1
Source dataset
uspto-grants-2011_12
Patent number
US08076487B2

Reaction notes

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