Water → HCID 22933709, compound

HRID 1269795Notes

Reaction equation

HRID 1269795 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N+:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[CH:3]2)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 113411-Bromo-2-nitrobenzeneHCID 11430Potassium CarbonateHCID 1014381H-Indazol-5-ol

Product 1

HCID 22933709HCID 22933709, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of the 1H-indazol-5-ol (300 mg, 2.24 mmol) obtained in Reference Example 4 in N,N-dimethylformamide (6 ml) were added 2-bromonitrobenzene (497 mg, 2.46 mmol) and potassium carbonate (402 mg, 2.91 mmol), and the resulting mixture was heated to 120° C. After 6 hours, the mixture was poured into water (20 ml) and extracted with ethyl acetate (20 ml×2). The organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 5-(2-nitrophenoxy)-1H-indazole (57 mg, 10%).

Workup

  1. extractionextracted with ethyl acetate (20 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe organic layer dried
  4. concentrationwas concentrated under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fe3db06749eb44e7aa48418ca580d89b
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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