Water → (E)-3-{2-[4-(4-methanesulfonylpiperazin-1-yl)-2-nitrophenyl]vinyl}-1H-indazole

HRID 1821404Notes

Reaction equation

HRID 1821404 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[Br-].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH2:32][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:24]1.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:18]=[CH:17][C:14](/[CH:15]=[CH:32]/[C:25]3[C:26]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[NH:23][N:24]=3)=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 866282144-(4-Methanesulfonylpiperazin-1-yl)-2-nitrobenzaldehydeHCID 178419401HCID 178419401, compound

Product 1

HCID 69000300(E)-3-{2-[4-(4-methanesulfonylpiperazin-1-yl)-2-nitrophenyl]vinyl}-1H-indazoleYield 102.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(4-methanesulfonylpiperazin-1-yl)-2-nitrobenzaldehyde (0.36 g, 1.1 mmol) obtained in Step 1 in methanol (5.0 mL), (1H-indazol-3-ylmethyl) triphenylphosphonium bromide (0.54 g, 1.1 mmol) and potassium carbonate (0.31 g, 2.3 mmol) were added, followed by stirring at room temperature for 1 hour. 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 filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to ethyl acetate) to obtain (E)-3-{2-[4-(4-methanesulfonylpiperazin-1-yl)-2-nitrophenyl]vinyl}-1H-indazole (0.48 g, 26%).

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 filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to ethyl acetate)

Sources & evidence

ORD record
ord-2c39364e6a674652a5a42917729f9a7a
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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