Potassium Carbonate → Methyl 2-(imidazo[1,2-b]pyridazin-6-ylthio)benzoate

HRID 2391559Notes

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

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 6-chloroimidazo[1,2-b]pyridazine (1536 mg, 10.0 mmol), methyl 2-mercaptobenzoate (1.788 mL, 13.0 mmol), potassium carbonate (4146 mg, 30.0 mmol) and N,N-dimethylformamide (20 mL) was stirred at 70° C. for 18 hr. To the reaction mixture was added methyl 2-mercaptobenzoate (0.963 mL, 7.0 mmol), and the mixture was stirred at 70° C. for 6 hr. The reaction mixture was concentrated under reduced pressure, the residue 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) and precipitated from diisopropyl ether to give the title compound (663 mg, 2.3 mmol, yield 23%) as a white solid.

Workup

stirringthe mixture was stirred at 70° C. for 6 hr
concentrationThe reaction mixture was concentrated under reduced pressure
additionthe residue was diluted with water
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)
customprecipitated from diisopropyl ether

Sources & evidence

ORD record: ord-0d388356a03c44c09ffda2fe2d54337a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273741B2

Reaction notes

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