Potassium Carbonate → (E)-3-[2-(2-benzyloxyphenyl)vinyl]-1H-indazole

HRID 1821319Notes

Reaction equation

HRID 1821319 reaction equation
[Br-].[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.[CH2:31]([O:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH:41]=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CO>[CH2:31]([O:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1/[CH:41]=[CH:11]/[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:2][N:3]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 3447842-(Benzyloxy)benzaldehydeHCID 516892Sodium BicarbonateHCID 178419401HCID 178419401, compound

Product 1

HCID 69002362(E)-3-[2-(2-benzyloxyphenyl)vinyl]-1H-indazoleYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1H-indazol-3-ylmethyl)triphenylphosphonium bromide (150 mg, 0.32 mmol) was dissolved in methanol (2 mL) and the solution was added with o-benzyloxybenzaldehyde (55 μL, 0.35 mmol) and potassium carbonate (88 mg, 0.63 mmol), followed by stirring at room temperature for 2 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution, and extracted with ethyl acetate. Then, the organic layer was sequentially washed with water and saturated brine, and was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in a mixed solvent of ethyl acetate/hexane (2/1) to obtain Compound 13 (39.3 mg, 38%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThen, the organic layer was sequentially washed with water and saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was triturated in a mixed solvent of ethyl acetate/hexane (2/1)

Sources & evidence

ORD record
ord-be15c0ab5667474a95c08be9745c149c
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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