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
Participants
| Role | Name | HCID | Charge |
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| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | N-[7-(4-bromo-2-methoxyphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine | HCID 21984710 | — |
| Solvent | Zinc | HCID 23994 | — |
| Product | 4-[3-[Di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-7-yl]-3-methoxybenzonitrile | HCID 21984566 | — |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07625925B2 |
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| Source dataset | uspto-grants-2009_12 |
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| ORD ID | ord-a8d3d2d455514d96ade7571b6a49bc23 |
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| Source note | uspto-grants-2009_12 |
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