Methanol → HCID 136200883, compound

HRID 1619666Notes

Reaction equation

HRID 1619666 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10](I)[CH:9]=2)=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17].C([Sn](CCCC)(CCCC)[C:25]1[CH:30]=[CH:29][N:28]=[N:27][CH:26]=1)CCC.[F-].[Cs+].CO>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]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:25]3[CH:30]=[CH:29][N:28]=[N:27][CH:26]=3)[CH:9]=2)=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17]

Participants

8

Reactant 4

HCID 887MethanolHCID 25953Cesium fluorideHCID 64097334-(Tributylstannyl)pyridazineHCID 58042312HCID 58042312, compound

Product 1

HCID 136200883HCID 136200883, compoundYield 64.3%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
45 °C

Procedure

4′-Chloro-3-iodo-3′-(trifluoromethyl)biphenyl-4-ol (Preparation 55, 167 mg, 0.42 mmol) was dissolved in acetonitrile (1 mL) and 4-(tributylstannyl)pyridazine (200 mg, 0.55 mmol), caesium fluoride (127 mg, 0.84 mmol), copper iodide (16 mg, 0.084 mmol) and tetrakis(triphenylphosphine)palladium (0) (46 mg, 0.04 mmol) were added. The reaction was stirred at 45° C. for 40 minutes and then partitioned between ethyl acetate (50 mL) and water (10 mL) containing 0.880 ammonia (1 mL). The mixture was stirred for 20 minutes. The ethyl acetate was separated, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica eluting with a gradient of dichloromethane:methanol: 0.880NH3 100:0:0 to 92:8:0.8 to give the title compound (95 mg, 0.27 mmol, 64%) as a white solid.

Workup

  1. custompartitioned between ethyl acetate (50 mL) and water (10 mL)
  2. additioncontaining 0.880 ammonia (1 mL)
  3. stirringThe mixture was stirred for 20 minutes
  4. customThe ethyl acetate was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed on silica eluting with a gradient of dichloromethane

Sources & evidence

ORD record
ord-0c7f160c675e45ec96662aa2bb4693df
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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