Potassium Carbonate → 3-(Imidazo[1,2-b]pyridazin-6-yloxy)aniline

HRID 1667955Notes

Reaction equation

HRID 1667955 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[NH2:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>[OH-].[Na+]>[N:10]1[CH:9]=[CH:8][N:6]2[C:5]=1[CH:4]=[CH:3][C:2]([O:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[NH2:11])=[N:7]2

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 13387N-methyl-2-pyrrolidoneHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-

Product 1

HCID 574410563-(Imidazo[1,2-b]pyridazin-6-yloxy)anilineYield 41.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-chloroimidazo[1,2-b]pyridazine (1536 mg, 10.0 mmol), 3-aminophenol (1419 mg, 13.0 mmol), potassium carbonate (4146 mg, 30.0 mmol) and N-methylpyrrolidone (10 mL) was stirred at 120° C. for 48 hr. The reaction mixture was diluted with 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with 1N aqueous sodium hydroxide solution and saturated brine, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=70/30→0/100), and precipitated from diisopropyl ether to give the title compound (932 mg, 41%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1N aqueous sodium hydroxide solution and saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=70/30→0/100)
  5. customprecipitated from diisopropyl ether

Sources & evidence

ORD record
ord-78fb6529b40140fca7bdb8ffc9b17633
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

Loading…