Hydrazine → 7-fluoro-6-(2-fluoro-phenylamino)-3-methyl-2H-indazole-5-carboxylic acid methyl ester

HRID 558229Notes

Reaction equation

HRID 558229 reaction equation
[C:1]([C:4]1[C:5](F)=[C:6]([F:22])[C:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=O)[CH3:2].[NH2:24][NH2:25]>CN(C=O)C>[CH3:12][O:11][C:9]([C:8]1[C:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:6]([F:22])[C:5]2[C:4](=[C:1]([CH3:2])[NH:24][N:25]=2)[CH:13]=1)=[O:10]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59519431Methyl 5-acetyl-2-(2-fluorophenylamino)-3,4-difluorobenzoate

Product 1

HCID 595194097-fluoro-6-(2-fluoro-phenylamino)-3-methyl-2H-indazole-5-carboxylic acid methyl esterYield 150.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 5-acetyl-2-(2-fluorophenylamino)-3,4-difluorobenzoate (500 mg, 1.55 mmol, from step D in example 3) in DMF (10 ml) was added hydrazine (0.06 mL, 1.85 mmol). After stirring at room temperature for 16 h, the reaction was quenched with NH4Cl solution and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford 740 mg (75%) of the title compound.

Workup

  1. customthe reaction was quenched with NH4Cl solution
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc778c4406fc4130a2b2e8e0016e70c3
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

Loading…