HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,6-Dibromopyridine → Tert-butyl 4-[3-(6-bromopyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,6-Dibromopyridine | HCID 12274 | — |
| Reactant | 1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate | HCID 16211673 | — |
| Reactant | 4-(3-Trimethylsilylprop-2-ynylidene)piperidine | HCID 57574982 | — |
| Reactant | 6-Methyl-3-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridine | HCID 86627349 | — |
| Reactant | tert-Butyl 4-(3-trimethylsilylprop-2-ynylidene)piperidin-1-carboxyate | HCID 87119414 | — |
| Product | Tert-butyl 4-[3-(6-bromopyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate | HCID 87641844 | 68% |
Reaction Steps
The title compound was prepared from Compound 2a (in place of Compound 274c) following the procedure described for the compound of Example 274, using 2,6-dibromopyridine instead of 1-bromo-3,5-difluorobenzene and adding 1 molar equivalent of tetrabutylammonium fluoride monohydrate to the starting reaction mixture. After the work-up, the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc gradient from 10:0 to 8:2 affording the title product. White solid. Yield: 68%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08518916B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-9cf7cd3d71874c2db06d7cbee74caaad |
| Source note | uspto-grants-2013_08 |