4-Fluorobenzonitrile → HCID 178509531, compound

HRID 503110Notes

Reaction equation

HRID 503110 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.FC1C=CC(C#N)=CC=1.[Br:21]N1C(=O)CCC1=O>CN(C)C=O>[Br:21][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]#[N:11])[CH:5]=2)[NH:1][N:2]=1

Participants

5

Reactant 3

HCID 145174-FluorobenzonitrileHCID 67184N-bromobutanimideHCID 111263841H-Indazole-5-carbonitrile

Product 1

HCID 178509531HCID 178509531, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 300 mg of a compound 1H-5-indazolecarbonitrile (synthesized from 4-fluorobenzonitrile according to the procedures described in literature, Tetrahedron Lett., 33, 7499 (1992) and Synthetic commun., 27, 1199 (1997)) in 3 ml dimethylformamide was added 392 mg of N-bromosuccinimide at room temperature, and the mixture was stirred at the same temperature for one day. After removing the solvent by distillation, the residue was added with 25 ml of ethyl acetate. The mixture was sequentially washed with half-saturated aqueous sodium hydrogencarbonate solution, water and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 440 mg of the title compound as pale red crystals.

Workup

  1. customAfter removing the solvent
  2. distillationby distillation
  3. additionthe residue was added with 25 ml of ethyl acetate
  4. washThe mixture was sequentially washed with half-saturated aqueous sodium hydrogencarbonate solution, water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3c41e472df1242bfb89a701dda4f1773
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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