HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Bromophenetole → 2-{4-[3-(3-Ethoxyphenyl)prop-2-ynylidene]piperidin-1-yl}-6-methyl-3-nitropyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Bromophenetole | HCID 75867 | — |
| 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 | — |
| Product | 2-{4-[3-(3-Ethoxyphenyl)prop-2-ynylidene]piperidin-1-yl}-6-methyl-3-nitropyridine | HCID 86627352 | 46% |
Reaction Steps
The title Compound was prepared from Compound 274c following the procedure described for the compound of Example 274 but using 3-ethoxybromobenzene 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 (SP1™-Biotage) eluting with PE-EtOAc gradient from PE:EtAc 1:0 to 8:2 affording the title product. Yellow solid. Yield: 46%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08518916B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-122d1bac94834940b0d2fe42f525318a |
| Source note | uspto-grants-2013_08 |