Water → HCID 178471076, compound

HRID 489408Notes

Reaction equation

HRID 489408 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]1[C:29]([C:30]#[N:31])=[C:28]([CH:32]=O)[NH:27][C:26]2=[N:34][NH:35][CH:36]=[C:25]12.O>C(COC)OC>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]1[C:29]([C:30]#[N:31])=[C:28](/[CH:32]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:27][C:26]2=[N:34][NH:35][CH:36]=[C:25]12

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 178510264HCID 178510264, compound

Product 1

HCID 178471076HCID 178471076, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of sodium hydride (94 mg) in dimethoxyethane (10 ml) was added ethyl diethylphosphonoacetate (528 mg) and the mixture was stirred at room temperature for 15 minutes. Under ice-cooling, 4-(2-chlorophenyl)-5-cyano-6-formyl-4,7-dihydro-2H-pyrazolo[3,4-b]pyridine (670 mg) was added to the mixture, and the mixture was stirred at the same temperature for 1 hour. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (1:1)) to give the title compound (560 mg) as yellow crystals.

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (1:1))

Sources & evidence

ORD record
ord-7eb80963a1ba4026923eac40cb862181
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Reaction notes

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