Sodium Hydroxide → 5-(3,5-bistrifluoromethylpyrazol-1-ylmethyl)-2-(3-chloropyridin-2-yl)-2H-pyrazole-3-carboxylic acid

HRID 41858Notes

Reaction equation

HRID 41858 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]([CH2:12][C:13]2[CH:14]=[C:15]([C:25]([O:27]C)=[O:26])[N:16]([C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][N:19]=3)[N:17]=2)[N:4]=1.[OH-].[Na+]>C(O)C.O>[F:30][C:2]([F:1])([F:29])[C:3]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]([CH2:12][C:13]2[CH:14]=[C:15]([C:25]([OH:27])=[O:26])[N:16]([C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][N:19]=3)[N:17]=2)[N:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86638528methyl 5-(3,5-bistrifluoromethylpyrazol-1-ylmethyl)-2-(3-chloropyridin-2-yl)-2H-pyrazole-3-carboxylate

Product 1

HCID 866385275-(3,5-bistrifluoromethylpyrazol-1-ylmethyl)-2-(3-chloropyridin-2-yl)-2H-pyrazole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 610 mg (1.34 mmol) of methyl 5-(3,5-bistrifluoromethylpyrazol-1-ylmethyl)-2-(3-chloropyridin-2-yl)-2H-pyrazole-3-carboxylate in 9 ml of ethanol is admixed dropwise with a solution of 699 mg (1.78 mmol) of sodium hydroxide in 7 ml of water. The mixture is stirred at room temperature for 2 hours and concentrated to about 5 ml on a rotary evaporator. This residue is admixed with 5 ml of tert-butyl methyl ether and the organic phase is subsequently washed with water. The combined aqueous phases are adjusted to a pH of about 3 with concentrated hydrochloric acid, with ice cooling, and are extracted with three times 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate and then the solvent is removed on a rotary evaporator.

Workup

  1. concentrationconcentrated to about 5 ml on a rotary evaporator
  2. washthe organic phase is subsequently washed with water
  3. extractionare extracted with three times 50 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-4fe1df9fc0cd45bba63aa8d634d50dab
Source dataset
uspto-grants-2013_09
Patent number
US08536092B2

Reaction notes

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