Sodium Carbonate → 63843-14-1

HRID 571964Notes

Reaction equation

HRID 571964 reaction equation
Cl[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5683453-Chlorocyclohex-2-en-1-oneHCID 27343783-Pyridinylboronic acid

Product 1

HCID 1340257163843-14-1

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium-DCM complex (313 mg, 0.383 mmol) was added to a stirred mixture of 8a (500 mg, 3.83 mmol), pyridin-3-yl-boronic acid (565 mg, 4.60 mmol) and sodium carbonate (2.87 mL of a 2M aq. solution, 5.74 mmol) in dioxane (14.0 mL) and water (2.00 mL). The resulting mixture was degassed and heated to 95° C. After 7 h, the reaction mixture was cooled to rt, diluted with EtOAc, filtered through a short column of Celite®, eluting copiously with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (0-90% EtOAc/hexanes as eluent) to afford the title compound, 8b. m/z (ES) 174 (MH)+

Workup

  1. customThe resulting mixture was degassed
  2. temperaturethe reaction mixture was cooled to rt
  3. additiondiluted with EtOAc
  4. filtrationfiltered through a short column of Celite®
  5. washeluting copiously with EtOAc
  6. washThe organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by column chromatography on silica gel (0-90% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-a8cb637dc19e429d8fb295052318e14f
Source dataset
uspto-grants-2015_05
Patent number
US09029377B2

Reaction notes

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