Water → N-[7-(2-Methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(2-pyridyl)amine

HRID 1865032

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[C:11]1[N:16]2[N:17]=[C:18]([S:21][CH3:22])[C:19]([NH2:20])=[C:15]2[CH:14]=[CH:13][CH:12]=1.CC(C)([O-])C.[Na+].O.Br[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[C:11]1[N:16]2[N:17]=[C:18]([S:21][CH3:22])[C:19]([NH:20][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)=[C:15]2[CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 120 °C

Procedure

After dissolving [7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (40 mg) in toluene (1 mL), 2-bromopyridine (0.013 mL), sodium t-butoxide (25 mg) and dichlorobis(tri-o-tolylphosphine)palladium complex (3 mg) were added and the mixture was heated and stirred at 120° C. for 5 hours. The mixture was cooled to room temperature, water was added, and extraction was performed with ethyl acetate. The organic layer washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and the title compound (12 mg) was obtained from the ethyl acetate:n-hexane (1:2) fraction as white crystals.

Workup

additionwere added
temperaturethe mixture was heated
temperatureThe mixture was cooled to room temperature
extractionextraction
washThe organic layer washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-1516e2e8483c4186ad7468c6d83d6771
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625925B2

Linked notes

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