HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2201833Generated: October 29, 2026
Dimethylformamide → 3,5-dichloro-4-(1H-pyrrolo[2,3-c]pyridin-3-ylcarbonyl)benzonitrile
https://huagongshe.com/reaction/2201833
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | (4-Bromo-2,6-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone | HCID 71061835 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3,5-dichloro-4-(1H-pyrrolo[2,3-c]pyridin-3-ylcarbonyl)benzonitrile | HCID 71618236 | 2% |
Reaction Steps
A mixture of (4-bromo-2,6-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone (100 mg, 0.27 mmol) in dimethylformamide (3 mL) was treated with zinc cyanide (25.2 mg, 0.21 mmol), tris(dibenzylideneacetone)dipalladium (0) (6.21 mg, 0.006 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (5.6 mg, 0.01 mmol) followed by heating at 130° C. for 16 hours. The reaction mixture was diluted with ethyl acetate, filtered over celite, and the filtrate was concentrated under vacuum. The crude compound was purified by LC-MS to afford 3,5-dichloro-4-(1H-pyrrolo[2,3-c]pyridin-3-ylcarbonyl)benzonitrile (2 mg, 2%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09364466B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-6a2d006854744bf4b2bd93c71bc61db9 |
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| Source note | uspto-grants-2016_06 |
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