Trifluoroacetic acid → 7-fluoro-6-(2-fluoro-4-iodophenylamino)-2,3-dimethyl-2H-indazole-5-carboxylic acid methyl ester

HRID 1161820Notes

Reaction equation

HRID 1161820 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:12]([F:22])[C:11]2[C:7](=[C:8]([CH3:24])[N:9]([CH3:23])[N:10]=2)[CH:6]=1)=[O:4].C1C(=O)N([I:32])C(=O)C1.C(O)(C(F)(F)F)=O>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([I:32])=[CH:17][C:16]=2[F:21])=[C:12]([F:22])[C:11]2[C:7](=[C:8]([CH3:24])[N:9]([CH3:23])[N:10]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 595194847-fluoro-6-(2-fluoro-phenylamino)-2,3-dimethyl-2H-indazole-5-carboxylic acid methyl ester

Product 1

HCID 595194157-fluoro-6-(2-fluoro-4-iodophenylamino)-2,3-dimethyl-2H-indazole-5-carboxylic acid methyl esterYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-fluoro-6-(2-fluoro-phenylamino)-2,3-dimethyl-2H-indazole-5-carboxylic acid methyl ester (141 mg, 0.43 mmol) in DMF (5 ml) were added NIS (144 mg, 0.64 mmol) and TFA (0.20 mL), and the reaction was stirred at room temp for 4 h. The crude was diluted with EtOAc and washed with H2O. The organic fraction is dried over MgSO4 and concentrated under reduced pressure. Silica gel chromatography (EtOAc:Hexanes=75:25) yielded 137 mg (70%) of the title compound as a yellow solid.

Workup

  1. washwashed with H2O
  2. dry with materialThe organic fraction is dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da0b33701bf64da4be996514706917dd
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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