Potassium Phosphate, Tribasic → HCID 70847647, compound

HRID 82174Notes

Reaction equation

HRID 82174 reaction equation
[C:1]([O:5][C:6](=[O:14])[CH2:7][N:8]1[CH:12]=[C:11](Br)[CH:10]=[N:9]1)([CH3:4])([CH3:3])[CH3:2].[CH:15]1(B(O)O)[CH2:17][CH2:16]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:15]1([C:11]2[CH:10]=[N:9][N:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:14])[CH:12]=2)[CH2:17][CH2:16]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 70847699tert-Butyl 2-(4-bromo-1H-pyrazol-1-yl)acetate

Product 1

HCID 70847647HCID 70847647, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Palladium acetate (215 mg, 0.957 mmol) was added to tert-butyl[4-bromo-1H-pyrazol-1-yl]acetate (5 g, 19.14 mmol) (see Preparation 86), cyclopropyl boronic acid (8.22 g, 95.74 mmol), potassium phosphate (8.12 g, 38.29 mmol) and tricyclohexylphosphine (537 mg, 1.91 mmol) in toluene: water (60 mL:15 mL). The mixture was degassed for 20 minutes then refluxed for 18 hours. The reaction mixture was filtered through Celite™, the filtrate was evaporated in vacuo and the residue was purified by column chromatography on silica gel (gradient of EtOAc:hexane 15:85) to afford the title compound as an off white solid in 21% yield, 1.3 g.

Workup

  1. customThe mixture was degassed for 20 minutes
  2. temperaturethen refluxed for 18 hours
  3. filtrationThe reaction mixture was filtered through Celite™
  4. customthe filtrate was evaporated in vacuo
  5. customthe residue was purified by column chromatography on silica gel (gradient of EtOAc:hexane 15:85)

Sources & evidence

ORD record
ord-a54aea3d03664d84bc456074aa89d50a
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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