Potassium Phosphate, Tribasic → HCID 57672419, compound

HRID 2101766Notes

Reaction equation

HRID 2101766 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](Cl)[CH:8]=[C:9]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])[CH:10]=1)=[O:4].[CH:21]1(B(O)O)[CH2:23][CH2:22]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])[C:8]([CH:21]2[CH2:23][CH2:22]2)=[CH:7][CH:6]=1)=[O:4]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 68822450HCID 68822450, compound

Product 1

HCID 57672419HCID 57672419, compoundYield 85.4%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a round bottom flask containing 13.2 (0.46 g, 1.56 mmol), cyclopropylboronic acid (0.40 g, 4.67 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.26 g, 0.638 mmol), palladium acetate (0.07 g, 0.31 mmol), and potassium phosphate tribasic (1.00 g, 4.71 mmol), was added a premixed solution of 1,4-dioxane (1.0 mL) and water (0.3 mL). The mixture was stirred at room temperature for 5 minutes and then heated to 88° C. and monitored with TLC. After 4 hours, the reaction was cooled to room temperature and diluted with EtOAc. The mixture was then filtered through a pad of silica gel (eluting with EtOAc) and concentrated under reduced pressure. The crude residue was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 25% EtOAc in hexanes) to yield a colorless oil 13.3 (0.4 g, 85% yield.) 1H NMR (400 MHz, CDCl3) δ ppm 7.99 (2H, m), 7.07 (1H, t, J=8.8 Hz), 6.96 (1H, d, J=8.2 Hz), 6.91 (2H, m), 3.89 (3H, s), 3.81 (3H, s), 1.84 (1H, dt, J=8.6, 4.3 Hz), 0.93 (2H, m), 0.75 (2H, m).

Workup

  1. temperatureheated to 88° C.
  2. waitAfter 4 hours
  3. temperaturethe reaction was cooled to room temperature
  4. filtrationThe mixture was then filtered through a pad of silica gel (eluting with EtOAc)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bb562914193246da8ec4a4f38abe7a1d
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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