Water → HCID 22933715, compound

HRID 1269841Notes

Reaction equation

HRID 1269841 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].C1(S)C=CC=CC=1.[N+](C1C=CC=CC=1S([O:26][C:27]1[C:28]([O:36][CH3:37])=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][N:31]=[CH:30]2)(=O)=O)([O-])=O.O>CN(C)C=O>[CH3:37][O:36][C:28]1[C:27]([OH:26])=[CH:35][CH:34]=[C:33]2[C:29]=1[CH:30]=[N:31][NH:32]2

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 10796Cesium carbonateHCID 86593612HCID 86593612, compound

Product 1

HCID 22933715HCID 22933715, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (45 mg, 0.137 mmol) and thiophenol (24 ml, 0.229 mmol) were added to a solution of 4-methoxy-1H-indazol-5-yl 2-nitrobenzenesulfonate (40 mg, 0.115 mmol) in N,N-dimethylformamide (1 ml) at 0° C. After 30 minutes, the reaction solution was poured into water (20 ml) and extracted with ethyl acetate (20 ml×2). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 4-methoxy-1H-indazol-5-ol (19 mg, 100%).

Workup

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

Sources & evidence

ORD record
ord-e66bf24d60014146a44a22d7cb29a519
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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