HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 10508Generated: October 26, 2026
5-Bromoisoquinoline → N-(tert-butoxycarbonyl)-N-methyl-N'-(5-isoquinolyl)-1,3-propylenediamine
https://huagongshe.com/reaction/10508
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 5-Bromoisoquinoline | HCID 736487 | — |
| Reactant | 2-(Di-tert-butylphosphino)biphenyl | HCID 2734215 | — |
| Reactant | tert-butyl N-(3-aminopropyl)-N-methylcarbamate | HCID 2756543 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | N-(tert-butoxycarbonyl)-N-methyl-N'-(5-isoquinolyl)-1,3-propylenediamine | HCID 21979883 | 85.1% |
Reaction Steps
Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (252 mg), tris(dibenzylideneacetone)palladium(0) (59 mg), 2-(di-tert-butylphosphino)biphenyl (74 mg), (3-aminopropyl)methylcarbamic acid tert-butyl ester (274 mg, Asta Tech), and sodium tert-butoxide (163 mg) in toluene was stirred with heating at 70° C. for 3 hours. The reaction mixture was returned to room temperature and purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (325 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07094789B2 |
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| Source dataset | uspto-grants-2006_08 |
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| ORD ID | ord-34859159c1f24492b072bc7bfbc36a45 |
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| Source note | uspto-grants-2006_08 |
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