Potassium Phosphate, Tribasic → HCID 87088131, compound

HRID 402763Notes

Reaction equation

HRID 402763 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:50][C:51]1[C:56]([F:57])=[C:55]([F:58])[CH:54]=[CH:53][C:52]=1B(O)O>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([O:10][C:7]1[CH:6]=[C:3]([CH:4]=[O:5])[C:2]([C:54]2[CH:53]=[CH:52][C:51]([F:50])=[C:56]([F:57])[C:55]=2[F:58])=[CH:9][CH:8]=1)[CH3:12]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27832802,3,4-Trifluorobenzeneboronic acidHCID 30164192-Bromo-5-ethoxybenzaldehydeHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 87088131HCID 87088131, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a degassed solution of 2-bromo-5-ethoxybenzaldehye (300 mg, 1.31 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (53.8 mg, 0.131 mmol; S-Phos ligand), palladium (II) acetate (14.7 mg, 0.065 mmol) in THF (8 mL) were added K3PO4 (834 mg, 3.93 mmol) and (2,3,4-trifluorophenyl)boronic acid (276, 1.57 mmol). Reaction mixture was stirred at 70° C. under a N2 atmosphere for 16 hours, cooled to room temperature and then filtered. The filtrate was concentrated by evaporation under reduced pressure. The residue was purified on a silica gel column eluting with 5 to 10% EtOAc in hexanes to provide the title intermediate (255 mg) as white solid.

Workup

  1. customReaction mixture
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  5. customThe residue was purified on a silica gel column
  6. washeluting with 5 to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-b6fd571bca3d487695db922439a541ef
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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