Potassium Carbonate → HCID 57441066, compound

HRID 2391564Notes

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.[OH:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>O>[N:10]1[CH:9]=[CH:8][N:6]2[C:5]=1[CH:4]=[CH:3][C:2]([O:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])=[N:7]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-chloroimidazo[1,2-b]pyridazine (1536 mg, 10.0 mmol), methyl 3-hydroxybenzoate (1978 mg, 13.0 mmol), potassium carbonate (4146 mg, 30.0 mmol) and N-methylpyrrolidone (10 mL) was stirred at 120° C. for 18 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=90/10→20/80). The objective fraction was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=60/40→0/100) and precipitated from diisopropyl ether to give the title compound (1722 mg, 6.4 mmol, yield 64%) as a white solid.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water
concentrationconcentrated under reduced pressure
customThe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=90/10→20/80)
concentrationThe objective fraction was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=60/40→0/100)
customprecipitated from diisopropyl ether

Sources & evidence

ORD record: ord-2ed8cae4be25495ab0772062e6e87fa0
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273741B2

Reaction notes

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