Water → 1H-Indazole

HRID 1821418Notes

Reaction equation

HRID 1821418 reaction equation
COCCN1CCN(C2C=CC(C=O)=C([N+]([O-])=O)C=2)CC1.[Br-].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](C[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:24]1.C(=O)([O-])[O-].[K+].[K+].O>CO>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[N:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 866282164-[4-(2-Methoxyethyl)piperazin-1-yl]-2-nitrobenzaldehydeHCID 178419401HCID 178419401, compound

Product 1

HCID 92211H-IndazoleYield 597.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[4-(2-methoxyethyl)piperazin-1-yl]-2-nitrobenzaldehyde (0.23 g, 0.68 mmol) obtained in Step 1 was dissolved in methanol (8.0 mL) and the solution was added with (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.32 g, 0.68 mmol) and potassium carbonate (0.19 g, 1.4 mmol), followed by stirring at room temperature for 1.5 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain (E)-3-{2-[4-(2-methoxyethyl)piperazin-1-yl]-2-nitrophenyl}vinyl}-1H-indazole (0.48 g, 100%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-1f935d76bff34ce4a68cc5c01c608219
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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