HCID 86723026, compound → HCID 86723027, compound

HRID 522315Notes

Reaction equation

HRID 522315 reaction equation
[I:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16]CC)=[O:15]>O1CCCC1.[Li+].[OH-].CO>[I:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 1

HCID 86723026HCID 86723026, compound

Product 1

HCID 86723027HCID 86723027, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-iodo-1-(3-fluorophenyl)-1H-pyrazole-4-carboxylate (589 mg, 1.64 mmol) was dissolved in a mixture of tetrahydrofuran (5 mL), 1.5 N LiOH (1.6 mL) and methanol (1.5 mL) and the mixture was stirred overnight. Most of the tetrahydrofuran was removed by gently blowing a stream of nitrogen over the reaction mixture. Water and 1 N HCl (2.4 mL) was added and the mixture was sonicated well to precipitate the carboxylic acid. The carboxylic acid was filtered and rinsed with water. After drying under vacuum, 5-iodo-1-(3-fluorophenyl)-1H-pyrazole-4-carboxylic acid was obtained (488 mg, 1.47 mmol, 90% yield). This material was used for the next step without further purification.

Workup

  1. customMost of the tetrahydrofuran was removed
  2. additionWater and 1 N HCl (2.4 mL) was added
  3. customthe mixture was sonicated well
  4. customto precipitate the carboxylic acid
  5. filtrationThe carboxylic acid was filtered
  6. washrinsed with water
  7. customAfter drying under vacuum

Sources & evidence

ORD record
ord-5773d953a604441bab9121e3ccaee288
Source dataset
uspto-grants-2016_05
Patent number
US09328116B2

Reaction notes

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