Potassium Carbonate → 3-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

HRID 512823Notes

Reaction equation

HRID 512823 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH3:9][N:10]1[CH:14]=[C:13](B2OC(C)(C)C(C)(C)O2)[CH:12]=[N:11]1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:13]2[CH:12]=[N:11][N:10]([CH3:9])[CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 673313,6-DichloropyridazineHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 545956073-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

In a two-neck flask was placed 3,6-dichloropyridazine (1.49 g, 10 mmol), 1-methylpyrazole-4-boronic acid pinacol ester (1.04 g, 5 mmol), K2CO3 (1.38 g, 10 mmol), and Pd(PPh3)4 (289 mg, 0.25 mmol). The resulting mixture was degassed and refilled with N2 (3 times). 1,4-Dioxane/H2O (9 mL/2 mL) was added and the resulting mixture was heated at 100° C. for 5 h. The resulting mixture was poured into EtOAc/H2O (30 mL/30 mL). The organic layer was washed with brine (30 mL), dried (Na2SO4), and filtered. The solvent was removed and the resulting residue was purified by column using 90-100% EtOAc/hexane as the eluent to yield 3-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine.

Workup

  1. customIn a two-neck flask was placed
  2. customThe resulting mixture was degassed
  3. additionrefilled with N2 (3 times)
  4. addition1,4-Dioxane/H2O (9 mL/2 mL) was added
  5. additionThe resulting mixture was poured into EtOAc/H2O (30 mL/30 mL)
  6. washThe organic layer was washed with brine (30 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customThe solvent was removed
  10. customthe resulting residue was purified by column

Sources & evidence

ORD record
ord-b02337b50d724fa5a9d06b2f50d14bfd
Source dataset
uspto-grants-2015_08
Patent number
US09102669B2

Reaction notes

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