3,6-Dichloropyridazine → HCID 59525729, compound

HRID 386117Notes

Reaction equation

HRID 386117 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[OH:9][C:10]([CH3:17])([CH3:16])/[CH:11]=[CH:12]/B(O)O>C1COCC1.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:3]=[N:4][C:5](/[CH:12]=[CH:11]/[C:10]([CH3:17])([OH:9])[CH3:16])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 673313,6-DichloropyridazineHCID 57416265[(1E)-3-Hydroxy-3-methylbut-1-en-1-yl]boronic acid

Product 1

HCID 59525729HCID 59525729, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3,6-dichloropyridazine (250 mg, 1.68 mmol) and [(1E)-3-hydroxy-3-methylbut-1-en-1-yl]boronic acid (218 mg, 1.68 mmol) in THF (5 mL) and 2.0 M NaHCO3 (1.70 mL) was added palladium tetrakis triphenylphosphine (97 mg, 0.084 mmol). The solution was degassed with nitrogen and heated to 85° C. overnight. The residue was worked up with EtOAc and water, dried with MgSO4, filtered, and concentrated. Column chromatography on silica gel 100% Hex to 100% EtOAc provided the title compound.

Workup

  1. customThe solution was degassed with nitrogen
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-20925361e56e4dc4aa1dc95f541273f5
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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