Triphenylphosphine → HCID 89253219, compound

HRID 927324Notes

Reaction equation

HRID 927324 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[O:14][C:9]2=[CH:10][N:11]=[CH:12][CH:13]=[C:8]2[CH:7]=1)CCC.Br[C:24]1[N:28]2[N:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]2=[N:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.[Cu]I>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]2[N:28]([C:24]([C:6]3[O:14][C:9]4=[CH:10][N:11]=[CH:12][CH:13]=[C:8]4[CH:7]=3)=[CH:25][N:26]=2)[N:29]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 46188132HCID 46188132, compound

Product 1

HCID 89253219HCID 89253219, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of crude 2-(tributylstannyl)furo[2,3-c]pyridine (1.9 g) in THF (20 mL) in an inert atmosphere was added 3-bromo-6-chloroimidazo[1,2-b]pyridazine (676 mg, 2.9 mmol), copper (I) iodide (55 mg, 0.29 mmol) bis(triphenylphosphine) palladium(II)chloride (102 mg, 0.145 mmol) and triphenylphosphine (38 mg, 0.145 mmol). The mixture was heated to reflux for 2 h. The solvent was removed in vacuum. The residue was dissolved in a mixture of dichloromethane and methanol, filtered through an aminophase-silica-gel column and the solvent was removed in vacuum. Silicagel chromatography gave a solid that was triturated with a mixture of ethyl acetate and hexane to give 343 mg of the title compound, which was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. customThe solvent was removed in vacuum
  4. dissolutionThe residue was dissolved in a mixture of dichloromethane and methanol
  5. filtrationfiltered through an aminophase-silica-gel column
  6. customthe solvent was removed in vacuum
  7. customSilicagel chromatography gave a solid
  8. customthat was triturated with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a569f21b3c534df59a56872564fd84f9
Source dataset
uspto-grants-2016_03
Patent number
US09290482B2

Reaction notes

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