Hydrochloric Acid → 4-(4-fluoro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic Acid

HRID 1961034Notes

Reaction equation

HRID 1961034 reaction equation
[F:1][C:2]1[CH:3]=[N:4][N:5]([CH3:16])[C:6]=1[C:7]1[CH:8]=[C:9]([C:12]([O:14]C)=[O:13])[S:10][CH:11]=1.Cl>C1COCC1.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[N:4][N:5]([CH3:16])[C:6]=1[C:7]1[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[S:10][CH:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57826631methyl 4-(4-fluoro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

Product 1

HCID 578265364-(4-fluoro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic Acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 4-(4-fluoro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (126 mg, 0.53 mmol) in THF (1 mL) and 6N NaOH (1 mL) was heated to 70° C. After 1 h, the solution was poured onto H2O and the pH was adjusted to ˜4 with aqueous HCl. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried (Na2SO4) and concentrated affording the title compound white was used directly without further purification: LCMS (ES) m/z=227 (M+H)+.

Workup

  1. additionthe solution was poured onto H2O
  2. extractionThe aqueous phase was extracted several times with DCM
  3. dry with materialthe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f2a7b0239dc341e39c342faa3b7d1296
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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