3-Bromo-6-chloroimidazo(1,2-b)pyridazine → HCID 71491984, compound

HRID 927322Notes

Reaction equation

HRID 927322 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[SnH3][C:13]1[O:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1>C1COCC1.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:13]3[O:21][C:20]4[C:15](=[N:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=3)=[CH:3][N:4]=2)[N:7]=1

Participants

6

Reactant 2

HCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 131735053HCID 131735053, compound

Product 1

HCID 71491984HCID 71491984, compoundYield 57.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In an inert atmosphere, 3.0 g (12.9 mmol) of 3-bromo-6-chloroimidazo[1,2-b]-pyridazine, 6.85 g (16.8 mmol) of the crude 2-stannylfuro[3,2-b]pyridine, 246 mg (1.29 mmol) copper (I) iodide and 453 mg (0.645 mmol) bis(triphenylphosphine) palladium(II)chloride in 100 mL of THF was stirred over night at 85° C. in a sealed pressure tube. The solvent was evaporated, the obtained solid was digested in dichloromethane/methanol and filtered off. The solid was washed with methanol and hexane to give 2 g of the title compound as solid material.

Workup

  1. customThe solvent was evaporated
  2. filtrationfiltered off
  3. washThe solid was washed with methanol and hexane

Sources & evidence

ORD record
ord-ecb23e5725274982b536f79ef834eda2
Source dataset
uspto-grants-2016_03
Patent number
US09290482B2

Reaction notes

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