Potassium Carbonate → HCID 59574401, compound

HRID 2092044Notes

Reaction equation

HRID 2092044 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[CH:8]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[CH3:9].[CH3:22]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.O1CCOCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH3:22])=[CH:6][C:7]=1[CH:8]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[CH3:9]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 11484080HCID 11484080, compound

Product 1

HCID 59574401HCID 59574401, compoundYield 19.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

2-[1-(3,6-Dichloropyridazin-4-yl)ethyl]isoindoline-1,3-dione (161 mg, 0.5 mmol), trimethylboroxine (0.209 mL, 1.5 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane complex (35.1 mg, 0.05 mmol) and potassium carbonate (82.9 mg, 0.6 mmol) were mixed with water (0.2 mL) and 1,4-dioxane (0.9 mL) and stirred at 110° C. for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the solvent was removed by vacuum distillation. The resulting residue was mixed with 4 M hydrogen chloride/1,4-dioxane (10 mL) and stirred at room temperature for 16 hours. After completion of the reaction, the reaction solution was mixed with water and extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by preparative thin-layer chromatography (hexane/ethyl acetate=1/1) to give the desired product (29 mg, 19% yield).

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled to room temperature
  3. customthe solvent was removed by vacuum distillation
  4. additionThe resulting residue was mixed with 4 M hydrogen chloride/1,4-dioxane (10 mL)
  5. stirringstirred at room temperature for 16 hours
  6. customAfter completion of the reaction
  7. extractionextracted with chloroform
  8. dry with materialthe extract was dried over anhydrous magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe resulting residue was purified by preparative thin-layer chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-00a030d08e3e4bc781aad948fb15e3a4
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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