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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1865019Generated: October 25, 2026

Dimethylformamide → 4-[3-[Di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-7-yl]-3-methoxybenzonitrile

https://huagongshe.com/reaction/1865019

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantEthyl AcetateHCID 8857—
ReactantN-[7-(4-bromo-2-methoxyphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamineHCID 21984710—
SolventZincHCID 23994—
Product4-[3-[Di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-7-yl]-3-methoxybenzonitrileHCID 21984566—

Reaction Conditions

Temperature95 °C

Reaction Steps

After dissolving N-[7-(4-bromo-2-methoxyphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine (60 mg) in N,N-dimethylformamide (0.26 mL), zinc cyamide (31 mg) and tetrakis (triphenylphosphine)palladium(0) complex (23 mg) were added, the mixture was heated and stirred at 95° C. for 12 hours and then cooled to room temperature, and ethyl acetate was added. After filtering out the precipitated insoluble portion, extraction was performed with ethyl acetate. The obtained organic layer washed with water and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:8) to obtain the title compound (32 mg) as a yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07625925B2
Source datasetuspto-grants-2009_12
ORD IDord-a8d3d2d455514d96ade7571b6a49bc23
Source noteuspto-grants-2009_12