Potassium Carbonate → 1h-Indazole,4-(2-fluoro-4-nitrophenoxy)-

HRID 16412Notes

Reaction equation

HRID 16412 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([OH:10])[C:4]=2[CH:3]=[N:2]1.[F:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1F.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1[O:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[N:2][NH:1]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 1357424501H-indazol-4-ol

Product 1

HCID 179793111h-Indazole,4-(2-fluoro-4-nitrophenoxy)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

100 mg (0.75 mmol) of 1H-indazol-4-ol (from example XXIV), 94 mg (0.64 mmol) of 3,4-difluoronitrobenzene and 103 mg (0.75 mmol) of potassium carbonate are suspended in 2 ml of anhydrous dimethylformamide, and the mixture is stirred at 50° C. for 5 hours. The reaction solution is then diluted with water and extracted 2× with ethyl acetate. The combined organic phases are dried over sodium sulfate. The solvent is removed under reduced pressure. The crude product is purified by preparative HPLC.

Workup

  1. extractionextracted 2× with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. customThe solvent is removed under reduced pressure
  4. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-c83dabd87f0f4c7791b6ee1bc5c18272
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

Loading…