Dichloromethane → HCID 86702325, compound

HRID 2279063Notes

Reaction equation

HRID 2279063 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.[CH3:12][O:13][C:14]1[C:19](B(O)O)=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].ClCCl>O.O1CCOCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:19]3[C:14]([O:13][CH3:12])=[N:15][CH:16]=[CH:17][CH:18]=3)=[CH:3][N:4]=2)[N:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 86702325HCID 86702325, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-6-chloroimidazo[1,2-b]pyridazine (Preparation 1b, 6.0 g, 25.81 mmol), (2-methoxypyridin-3-yl)boronic acid (3.3 g, 21.58 mmol), cesium carbonate (30 mL of a 2M solution in water, 60 mmol) and 1,4-dioxane (250 mL) in a Schlenk vial was subjected to three cycles of evacuation backfilling with argon. [1,1′-Bis(diphenyl phosphino)ferrocene]-dichloropalladium(II) complex with dichloromethane (1:1) (1.8 g, 2.16 mmol) was then added and the resulting mixture was again subjected to three further cycles of evacuation backfilling before being heated at 100° C. for 2 hours. Subsequently, the reaction was cooled down, diluted with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was treated with ethyl acetate and the solid formed was filtered, washed with dichloromethane and dried in vacuo to yield the title compound (3.5 g, 62%) as a yellow solid.

Workup

  1. temperatureSubsequently, the reaction was cooled down
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customthe solvent removed under reduced pressure
  5. additionThe residue was treated with ethyl acetate
  6. customthe solid formed
  7. filtrationwas filtered
  8. washwashed with dichloromethane
  9. customdried in vacuo

Sources & evidence

ORD record
ord-9b319f63980f4548b22bd106e6415835
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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