Lithium Hydroxide → 7-fluoro-6-(2-fluoro-4-iodophenylamino)-2,3-dimethyl-2H-indazole-5-carboxylic acid

HRID 1161821Notes

Reaction equation

HRID 1161821 reaction equation
C[O:2][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=2[F:22])=[C:12]([F:23])[C:11]2[C:7](=[C:8]([CH3:25])[N:9]([CH3:24])[N:10]=2)[CH:6]=1)=[O:4].[Li+].[OH-]>C1COCC1.O>[F:23][C:12]1[C:11]2[C:7](=[C:8]([CH3:25])[N:9]([CH3:24])[N:10]=2)[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=1[F:22]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 595194157-fluoro-6-(2-fluoro-4-iodophenylamino)-2,3-dimethyl-2H-indazole-5-carboxylic acid methyl ester

Product 1

HCID 595194507-fluoro-6-(2-fluoro-4-iodophenylamino)-2,3-dimethyl-2H-indazole-5-carboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-fluoro-6-(2-fluoro-4-iodophenylamino)-2,3-dimethyl-2H-indazole-5-carboxylic acid methyl ester (137 mg, 0.30 mmol) in a mixture of THF (10 ml) and H2O (5 ml) was added a solution of LiOH (1.50 mL, 1M in H2O, 1.50 mmol). After stirring at room temperature for 4 h, the reaction was concentrated, acidified with 1 M HCl solution, and extracted with EtOAc (2×20 ml). The organic solution was dried over MgSO4 and concentrated to give 126 mg (96%) the title compound as an orange solid.

Workup

  1. concentrationthe reaction was concentrated
  2. extractionextracted with EtOAc (2×20 ml)
  3. dry with materialThe organic solution was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f40664350c5c4df3ad3588047663c1f6
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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