Cesium fluoride → HCID 136200871, compound

HRID 1619676Notes

Reaction equation

HRID 1619676 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]=[C:12]([F:16])[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.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[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][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 64097334-(Tributylstannyl)pyridazineHCID 58042325HCID 58042325, compound

Product 1

HCID 136200871HCID 136200871, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

2-Chloro-3′-fluoro-5-iodobiphenyl-4-ol (Preparation 68, 480 mg, 1.38 mmol) and 4-(tributylstannyl)pyridazine (610 mg, 1.65 mmol) were dissolved in degassed acetonitrile (7 mL). Caesium fluoride (418 mg, 2.75 mmol) was added and the mixture further degassed. Tetrakis(triphenylphosphine) palladium (0) (159 mg, 0.14 mmol) and copper (I) iodide (79 mg, 0.41 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 anhydrous MgSO4, filtered and evaporated. The residue was purified by silica gel column chromatography (20% heptane in ethyl acetate) followed by trituration with dichloromethane to give the title compound (98 mg, 24%) as a white 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 anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography (20% heptane in ethyl acetate)

Sources & evidence

ORD record
ord-6481d0512a6b4f40bdb12e782b7b3f68
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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