Water → methyl (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoate

HRID 2378713Notes

Reaction equation

HRID 2378713 reaction equation
[I-].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:3]1.[CH:31]([C:33]1[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=1)=O.C(=O)([O-])[O-].[K+].[K+].O>CO>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:11]=[CH:31]/[C:33]2[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=2)=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15294Methyl 4-FormylbenzoateHCID 178506551HCID 178506551, compound

Product 1

HCID 11952156methyl (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoateYield 51.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1H-indazol-3-ylmethyl)triphenylphosphonium iodide (3.20 g, 6.15 mmol) obtained in Step 4 was dissolved in methanol (60 mL), and the solution was added with methyl p-formylbenzoate (1.00 g, 6.09 mmol) and potassium carbonate (2.55 g, 18.5 mmol), followed by stirring at room temperature overnight. The reaction mixture was added with water, and was extracted with ethyl acetate, then the organic layer was washed with saturated brine, and was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by thin-layer chromatography (chloroform/methanol=15/1), was further triturated in mixed solvent of ethyl acetate/diisopropyl ether to obtain methyl (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoate (0.87 g, 51%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by thin-layer chromatography (chloroform/methanol=15/1)
  6. customwas further triturated in mixed solvent of ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-2a64e1a175e6432188fd03bd3ed63601
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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