Potassium Phosphate, Tribasic → HCID 16097736, compound

HRID 1993915Notes

Reaction equation

HRID 1993915 reaction equation
Br[C:2]1[C:3](=[O:17])[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]([CH3:10])[C:6]=1[CH:7]1[CH2:9][CH2:8]1.[CH:18]1(B(O)O)[CH2:20][CH2:19]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:18]1([C:2]2[C:3](=[O:17])[N:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:5]([CH3:10])[C:6]=2[CH:7]2[CH2:9][CH2:8]2)[CH2:20][CH2:19]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 68676898HCID 68676898, compound

Product 1

HCID 16097736HCID 16097736, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

Into a sealable tube under argon was added 4-bromo-5-cyclopropyl-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one (2.59 g), cyclopropylboronic acid (1.23 g), potassium phosphate (8.18 g), tricyclohexyl phosphine (0.30 g), toluene (50 mL) and water (3.2 mL). To this was added palladium acetate (0.11 g) and the tube was sealed and stirred at 100° C. for 4 days. The reaction vessel was then cooled and then diluted with water/EtOAc. The phases were separated and the aqueous phase was extracted with further EtOAc. The combined organic phases were washed with brine, dried over sodium sulfate and evaporated in vacuo to afford a crude residue. Flash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane afforded the desired 4,5-dicyclopropyl-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one which was further purified by crystallization from EtOAc/pentante to give 1.12 g of the desired title compound as a white crystalline solid. MS (ESI+): 255.3 ([M+H]+).

Workup

  1. customthe tube was sealed
  2. temperatureThe reaction vessel was then cooled
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with further EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customto afford a crude residue
  9. washFlash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane

Sources & evidence

ORD record
ord-dd9cc64426cd465c966edc9458a7c475
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

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