Potassium Phosphate, Tribasic → HCID 57706268, compound

HRID 404341Notes

Reaction equation

HRID 404341 reaction equation
[CH3:1][C:2]1([CH3:26])[C:6]([C:7]2[CH:8]=[C:9]([CH:14]=[C:15]([F:25])[C:16]=2OS(C(F)(F)F)(=O)=O)[C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH2:4][CH2:3]1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[F:56][C:57]1[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[CH:59][C:58]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:26][C:2]1([CH3:1])[C:6]([C:7]2[CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[CH:14]=[C:15]([F:25])[C:16]=2[C:58]2[CH:59]=[C:60]([O:63][CH3:64])[CH:61]=[CH:62][C:57]=2[F:56])=[CH:5][CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57706468HCID 57706468, compound

Product 1

HCID 57706268HCID 57706268, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A stirred mixture of T10.6 (0.9464 g, 2.39 mmol), ground S-Phos (0.1977 g, 0.482 mmol), palladium acetate (0.0555 g, 0.247 mmol), 2-fluoro-5-methoxyphenylboronic acid (0.8114 g, 4.77 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), and potassium phosphate tribasic (1.2888 g, 6.072 mmol) in dry DMF (7.000 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to 75° C. After 21 hours, the reaction was cooled to room temperature, diluted with water and extracted three times with EtOAc. The combined organic layers were washed twice with brine. After drying over anhydrous sodium sulfate and filtering, the organic solvent was removed under reduced pressure. The residue was purified on an 80 g column of silica gel (0-20% EtOAc in hexanes) to afford T10.7 as a colorless oil that was used as is without further purification (850.5 mg, 95% yield). MS ESI (pos.) m/e: 373.0 (M+H)+.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layers were washed twice with brine
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. filtrationfiltering
  6. customthe organic solvent was removed under reduced pressure
  7. customThe residue was purified on an 80 g column of silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fc8ffdc450a24340b685ad9e25678123
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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