Sodium hydride → HCID 86761821, compound

HRID 2090828Notes

Reaction equation

HRID 2090828 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][NH:4][N:3]=1.[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:1][C:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=2)[N:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 178498883HCID 178498883, compound

Product 1

HCID 86761821HCID 86761821, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-methyl-1H-pyrazole-4-carboxylate (5.3 g) synthesized above in dimethylformamide (70 mL) was added sodium hydride (1.9 g, 60% in oil) at 0° C., and the mixture was stirred for 10 min. 2-Chloro-5-trifluoromethylpyridine (7.5 g) was added, and the mixture was stirred at room temperature overnight. Aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio) to give the title object compound (3.3 g, 31%) as a pale-yellow solid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio)

Sources & evidence

ORD record
ord-db64f469f0ed4c4786c0252196732629
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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