Water → HCID 86602666, compound

HRID 1445542Notes

Reaction equation

HRID 1445542 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10](=[O:18])[NH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]#[CH:27].O>C(#N)C>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]([O:18][CH2:27][C:26]#[CH:25])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 21113391Ethyl 2-(3-chloro-2-pyridinyl)-2,5-dihydro-5-oxo-1H-pyrazole-3-carboxylate2×

Product 1

HCID 86602666HCID 86602666, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 1-(3-chloro-2-pyridinyl)-2,3-dihydro-3-oxo-1H-pyrazole-5-carboxyate (i.e. the product of Example 1, Step B) (0.5 g, 1.9 mmol) in acetonitrile (20 mL) was added potassium carbonate (0.6 g, 3.8 mmol) and propargyl bromide (1.0 mL, 9.4 mmol). The reaction mixture was heated at reflux for 15 minutes. The mixture was then cooled and treated with water and extracted with a 1:1 mixture of diethyl ether and ethyl acetate. The organic extracts were then washed with a saturated solution of sodium chloride and dried over magnesium sulfate. The extract was concentrated to dryness on a rotary evaporator and chromatographed on silica gel using hexane/ethyl acetate (7:3) as eluent to isolate the title compound (0.45 g, 95% purity) as a red oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 15 minutes
  3. temperatureThe mixture was then cooled
  4. extractionextracted with a 1:1 mixture of diethyl ether and ethyl acetate
  5. washThe organic extracts were then washed with a saturated solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe extract was concentrated to dryness on a rotary evaporator
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-0bb6912feae549758da9eb1da76480e9
Source dataset
uspto-grants-2010_02
Patent number
US07666882B2

Reaction notes

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