Potassium Carbonate → HCID 57654580, compound

HRID 1921657Notes

Reaction equation

HRID 1921657 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[C:9]([O:13][C:14]([N:16]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:18]=[N:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:9]([O:13][C:14]([N:16]1[CH:20]=[C:19]([C:5]2[N:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:18]=[N:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 673313,6-DichloropyridazineHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate

Product 1

HCID 57654580HCID 57654580, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3,6-dichloro-pyridazine (1.06 g, 6.98 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester (1.47 g, 5.0 mmol) in 2.0 M potassium carbonate (10 mL, 20 mmol) and 1,4-dioxane (40 mL) was degassed by house vacuum for 15 min followed by bubbling with argon for ˜10 min, Peppsi-ipr (340 mg, 0.5 mmol) was then added. After flushing with argon for another ˜10 min, the mixture was heated at 70° C. for 4 h and allowed to cool to room temperature. The solid was removed by filtration through Celite, and the filtrate was separated. The aqueous solution was extracted with CH2Cl2 and the combined organic phases were dried over Na2SO4, concentrated, and purified by column to provide 0.65 g desired product (46%). 1H NMR (DMSO) δ 9.08 (s, 1H), 8.47 (s, 1H), 8.31 (d, J=9.0 Hz, 1H), 8.01 (d, J=9.0 Hz, 1H), 1.59 (s, 3H); MS (ES) m/z 280.8(M+H+).

Workup

  1. customwas degassed by house vacuum for 15 min
  2. customby bubbling with argon for ˜10 min
  3. additionPeppsi-ipr (340 mg, 0.5 mmol) was then added
  4. customAfter flushing with argon for another ˜10 min
  5. temperatureto cool to room temperature
  6. customThe solid was removed by filtration through Celite
  7. customthe filtrate was separated
  8. extractionThe aqueous solution was extracted with CH2Cl2
  9. dry with materialthe combined organic phases were dried over Na2SO4
  10. concentrationconcentrated
  11. custompurified by column

Sources & evidence

ORD record
ord-012ff3bf68e547549de513ee87066560
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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