Water → 3-(3-Fluoro-phenyl)-6-methoxy-1H-indazole-5-carbonitrile

HRID 503157Notes

Reaction equation

HRID 503157 reaction equation
F[C:2]1[C:9]([C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:19][CH3:20])[CH:3]=1.O.[NH2:22][NH2:23].O>O1CCCC1.CO>[F:17][C:13]1[CH:12]=[C:11]([C:10]2[C:9]3[C:2](=[CH:3][C:4]([O:19][CH3:20])=[C:5]([C:6]#[N:7])[CH:8]=3)[NH:23][N:22]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 22261035HCID 22261035, compound

Product 1

HCID 222607803-(3-Fluoro-phenyl)-6-methoxy-1H-indazole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A total of 203 mg of 4-fluoro-5-(3-fluoro-benzoyl)-2-methoxy-benzonitrile obtained in Production Example II-1-c was dissolved in 3 ml of tetrahydrofuran and 3 ml of methanol, 7.4 ml of hydrazine monohydrate was added at room temperature under stirring, and the mixture was stirred at room temperature for 14 hours. Then, water was added and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate and the solvent was evaporated. The resulting crystals were washed with diethyl ether, to give 172 mg of the title compound as pale yellow crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe resulting organic layer was washed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. washThe resulting crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-7b01830d492b4a1b800c43e578609885
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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