Hydrochloric Acid → 5-Fluoro-1-isopropyl-1H-indazole-3-carboxylic acid

HRID 602480Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([CH3:13])[CH3:12])[N:6]=[C:5]2[C:14]([O:16]CC)=[O:15].[OH-].[Na+].Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([CH3:12])[CH3:13])[N:6]=[C:5]2[C:14]([OH:16])=[O:15]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of ethyl 5-fluoro-1-isopropyl-1H-indazole-3-carboxylate (125 mg, 0.5 mmol, step 1 of Example 11) in tetrahydrofuran (8 mL) was added 1N aqueous sodium hydroxide solution (1.0 mL, 1.0 mmol) at room temperature. The resulting mixture was stirred at 60° C. for 20 h. The mixture was acidified with 2 N hydrochloric acid (1 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 106 mg (95%) of the title compound as a white amorphous solid.

Workup

extractionextracted with ethyl acetate (50 mL×3)
dry with materialThe combined organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-891ac852b0444740ab4ae449682ea1ed
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906532B2

Reaction notes

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