Potassium Carbonate → HCID 178434285, compound

HRID 16394Notes

Reaction equation

HRID 16394 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[CH3:12][C:13]1[C:21]2[C:20]([OH:22])=[CH:19][CH:18]=[CH:17][C:16]=2[NH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[O:22][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:21]=1[C:13]([CH3:12])=[N:14][NH:15]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 178434282HCID 178434282, compound

Product 1

HCID 178434285HCID 178434285, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

100 mg (0.63 mmol) of 3,4-difluoronitrobenzene, 93.1 mg (0.63 mmol) of 3-methyl-1H-indazol-4-ol (from example I) and 95.6 mg (0.69 mmol) of potassium carbonate are suspended in 5 ml of anhydrous dimethylformamide and stirred at 50° C. for five hours. The reaction solution is then diluted with water and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by column chromatography. The mobile phase used is a mixture of cyclohexane and ethyl acetate (1:1).

Workup

  1. extractionextracted twice 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 residue is purified by column chromatography
  5. additiona mixture of cyclohexane and ethyl acetate (1:1)

Sources & evidence

ORD record
ord-a1183f51de954c63b1791ecc9fd75ad1
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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