Potassium Phosphate, Tribasic → ethyl [(diphenylmethylene)amino](1-methyl-1H-pyrazol-4-yl)acetate

HRID 923455Notes

Reaction equation

HRID 923455 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:22]1[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:1]1([C:7](=[N:8][CH:9]([C:22]2[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 1674331H-Pyrazole, 4-bromo-1-methyl-HCID 319508Ethyl 2-(diphenylmethyleneamino)acetate

Product 1

HCID 118318070ethyl [(diphenylmethylene)amino](1-methyl-1H-pyrazol-4-yl)acetateYield 10%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2.54 g of ethyl N-(diphenylmethylene)glycinate in 15 ml of toluene were added 1.52 g of 4-bromo-1-methyl-1H-pyrazole, 522 mg of bis(tri-tert-butylphosphine)palladium(0), and 6 g of tripotassium phosphate, followed by stirring at 100° C. for 12 hours. The reaction mixture was left to be cooled to room temperature and then filtered over Celite, and the filtrate was concentrated under reduced pressure. To the obtained residue was added water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 328 mg of ethyl [(diphenylmethylene)amino](1-methyl-1H-pyrazol-4-yl)acetate.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled to room temperature
  3. filtrationfiltered over Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the obtained residue was added water
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was then evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-559184ee7e2048259b6175842544823b
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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