Cesium fluoride → HCID 136200873, compound

HRID 1619680Notes

Reaction equation

HRID 1619680 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5](I)=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.C([Sn](CCCC)(CCCC)[C:22]1[CH:27]=[CH:26][N:25]=[N:24][CH:23]=1)CCC.[F-].[Cs+]>C(#N)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([C:22]2[CH:27]=[CH:26][N:25]=[N:24][CH:23]=2)=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 64097334-(Tributylstannyl)pyridazineHCID 580423282-Chloro-4'-fluoro-5-iodobiphenyl-4-ol

Product 1

HCID 136200873HCID 136200873, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

2-Chloro-4′-fluoro-5-iodobiphenyl-4-ol (Preparation 72, 553 mg, 1.59 mmol) and 4-(tributylstannyl)pyridazine (703 mg, 1.90 mmol) were dissolved in degassed acetonitrile (8 mL). Caesium fluoride (482 mg, 3.17 mmol) was added and the mixture further degassed. Tetrakistriphenylphosphinepalladium (0) (183 mg, 0.16 mmol) and copper (I) iodide (91 mg, 0.48 mmol) were added and the reaction heated at 50° C. for 2 hours. The reaction mixture was cooled and filtered through celite, washing with ethyl acetate. The organic solution was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by trituration with hot ethyl acetate to give the title compound (151 mg, 32%) as a beige solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through celite
  3. washwashing with ethyl acetate
  4. washThe organic solution was washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by trituration with hot ethyl acetate

Sources & evidence

ORD record
ord-b81634f8ae9544489e3f18bae9db232d
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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