Water → HCID 22260932, compound

HRID 503122Notes

Reaction equation

HRID 503122 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[F:17][C:18]1[CH:19]=[C:20]([C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([CH:33]=O)[CH:31]=3)[N:26]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[N:25]=2)[CH:21]=[CH:22][CH:23]=1.O>CN(C)C=O>[CH2:13]([O:12][C:10](=[O:11])/[CH:9]=[CH:33]/[C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[N:26]([C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])[N:25]=[C:24]2[C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([F:17])[CH:19]=1)[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 22260783HCID 22260783, compound

Product 1

HCID 22260932HCID 22260932, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.11 ml ethyl diethylphosphonoacetate in 5 ml N,N-dimethylformamide was added 20 mg of sodium hydride (60% oily) under ice-cooling, and the mixture was stirred for 15 minutes. To the reaction mixture was added a solution of 150 mg of tert-butyl 3-(3-fluorophenyl)-5-formyl-1H-1-indazolecarboxylate in 1 ml N,N-dimethylformamide, followed by stirring at room temperature for 30 minutes. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:10), to give 0.16 g of tert-butyl 5-[(E)-3-ethoxy-3-oxo-1-propenyl]-3-(3-fluorophenyl)-1H-1-indazolecarboxylate as a colorless oil. This product was dissolved in 2 ml of tetrahydrofuran, 0.1 ml of 5 N hydrochloric acid was added and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate for two times. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 0.14 g of the title compound as a colorless powder.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 30 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified
  8. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:10)

Sources & evidence

ORD record
ord-66e15208e504434ebd52f6f6da60a00e
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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