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

HRID 2391266Notes

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

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

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

Sources & evidence

ORD record: ord-7d9eac0d96044c539de33be1c30f6d8b
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273741B2

Reaction notes

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