HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1487675Generated: November 1, 2026
Dichloromethane → 4-(2-chloro-4-(3-cyanocyclobutoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-N-methylbenzamide
https://huagongshe.com/reaction/1487675
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide | HCID 17750267 | — |
| Reactant | 3-((2-Chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)cyclobutanecarbonitrile | HCID 86726501 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | 4-(2-chloro-4-(3-cyanocyclobutoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-N-methylbenzamide | HCID 86726502 | 50% |
Reaction Steps
3-((2-Chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)cyclobutanecarbonitrile (1 equiv), N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (1.15 equiv), sodium carbonate (3 equiv) and [1,1′-bisdiphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (0.1 equiv) suspended in 1,4-dioxane/water, and flushed with nitrogen, were stirred at 85° C. for 2 h. The reaction mixture was purified using silica gel chromatography (0 to 100% ethyl acetate in hexane) to give the title compound (50% yield). MS (ESI) m/z 512.3 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428509B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-4f39f4175f9e45d9b8d070a0773af856 |
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| Source note | uspto-grants-2016_08 |
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