Potassium Carbonate → HCID 68999815, compound

HRID 1821413Notes

Reaction equation

HRID 1821413 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[C:8]([N+:14]([O-:16])=[O:15])[CH:7]=1.[Br-].[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([CH2:27][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:19]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9](/[CH:10]=[CH:27]/[C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[NH:18][N:19]=2)=[C:8]([N+:14]([O-:16])=[O:15])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20026310HCID 20026310, compoundHCID 178419401HCID 178419401, compound

Product 1

HCID 68999815HCID 68999815, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(2-methoxyethoxy)-2-nitrobenzaldehyde (27 mg, 0.12 mmol) obtained in Step 1 in methanol (1.0 mL) was added with (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (57 mg, 0.12 mmol) and potassium carbonate (33 mg, 0.24 mmol), followed by stirring at room temperature for 1.5 hours. The reaction mixture was washed 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 (ethyl acetate) to obtain (E)-3-{2-[4-(2-methoxyethoxy)-2-nitrophenyl]vinyl}-1H-indazole (0.04 g, 100%).

Workup

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

Sources & evidence

ORD record
ord-38574ca2f85a4ed3abad9794954aadd6
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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