Cesium fluoride → HCID 136200887, compound

HRID 1619683Notes

Reaction equation

HRID 1619683 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][CH:13]=[CH:12][C:11]=1[F:16].C([Sn](CCCC)(CCCC)[C:22]1[CH:27]=[CH:26][N:25]=[N:24][CH:23]=1)CCC.[F-].[Cs+]>C(#N)C.[Cu](I)I.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]>[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][CH:13]=[CH:12][C:11]=1[F:16]

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 64097334-(Tributylstannyl)pyridazineHCID 58042353HCID 58042353, compound

Product 1

HCID 136200887HCID 136200887, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

2-Chloro-2′-fluoro-5-iodobiphenyl-4-ol (Preparation 75, 610 mg, 1.76 mmol) was dissolved in acetonitrile (3 mL) and 4-(tributylstannyl)pyridazine (843 mg, 2.28 mmol), caesium fluoride (533 mg, 3.51 mmol), copper iodide (67 mg, 0.35 mmol) and tetrakis(triphenylphosphine)palladium (0) (204 mg, 0.176 mmol) were added. The reaction was stirred at 80° C. for 18 hours and then the cooled reaction mixture was partitioned between ethyl acetate (100 mL) and water. The organic layer was separated and dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel eluting with heptane:ethyl acetate 1:1 to 100% ethyl acetate. Fractions containing product were evaporated and then triturated with dichloromethane to give the title compound (210 mg, 40%) as a yellow solid

Workup

  1. customthe cooled reaction mixture
  2. customwas partitioned between ethyl acetate (100 mL) and water
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on silica gel eluting with heptane
  8. additionFractions containing product
  9. customwere evaporated
  10. customtriturated with dichloromethane

Sources & evidence

ORD record
ord-17a5ceef0400455c902827d9f2b5f37d
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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