HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1479540Generated: October 31, 2026
Triethylamine → 10-Methylbenzo[f][1,7]naphthyridin-5-amine
https://huagongshe.com/reaction/1479540
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3,5-Dichloro-2-cyanopyridine | HCID 2769699 | — |
| Reactant | 5-Ethynyl-1H-indole | HCID 17842585 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 10-Methylbenzo[f][1,7]naphthyridin-5-amine | HCID 58213720 | 4% |
| Product | 5-((1H-indol-5-yl)ethynyl)-3-chloropicolinonitrile | HCID 66892311 | — |
Reaction Steps
To a round bottom flask capped with septa was added 5-ethynyl-1H-indole (from the previous step) (1.1 eq), 3,5-dichloropicolinonitrile (1 eq.), triethylamine (5 eq.), and anhydrous DMF (0.2 M). Vacuumed and nitrogen flushed for three times. CuI (0.05 eq.) and bis(triphenylphosphine)dichloro-palladium(II) (0.05 eq) were added. The septum was replaced with a refluxing condenser and the flask was heated at 60° C. overnight under nitrogen atmosphere. Upon completion of the reaction as monitored by TLC, the content of the flask was loaded onto a large silica gel column pretreated with hexanes. Flash chromatography (silica gel, hexanes:EtOAc (1:4%)) afforded the product 5-((1H-indol-5-yl)ethynyl)-3-chloropicolinonitrile.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09408907B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-54c7d78992ca4526a8ac0b24bbd2f662 |
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| Source note | uspto-grants-2016_08 |
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