Hydrochloric Acid → 6-Fluoro-3-[(E)-2-(thiophen-2-yl)-vinyl]-1H-indazole-5-carboxylic Acid

HRID 34032Notes

Reaction equation

HRID 34032 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[F:14])[NH:10][N:9]=[C:8]2/[CH:15]=[CH:16]/[C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)=[O:4].[OH-].[Na+].Cl>O1CCCC1>[F:14][C:13]1[CH:12]=[C:11]2[C:7]([C:8](/[CH:15]=[CH:16]/[C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)=[N:9][NH:10]2)=[CH:6][C:5]=1[C:3]([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59797280HCID 59797280, compound

Product 1

HCID 597969066-Fluoro-3-[(E)-2-(thiophen-2-yl)-vinyl]-1H-indazole-5-carboxylic AcidYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 60 mg of 6-fluoro-3-[(E)-2-(thiophen-2-yl)-vinyl]-1H-indazole-5-carboxylic acid methyl ester obtained by Example 142 in a mixture of 2 mL tetrahydrofuran/0.5 mL methanol was added 0.5 mL of 5N sodium hydroxide aqueous solution, and stirred at 50° C.-55° C. for 6 hours. The reaction solution was made acidic with 1N hydrochloric acid, and extracted with 15 mL of ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, to afford 53 mg of the title compound as bright yellow crystals.

Workup

  1. extractionextracted with 15 mL of ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-10ba1a887c3945ecbea65e53c09935da
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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