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

HRID 2392001Notes

Reaction equation

HRID 2392001 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-a384611344814f35aa4bd7487529e918
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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