HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-(3-Bromophenyl)acetamide → 3-{3-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}phenylacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-(3-Bromophenyl)acetamide | HCID 12123 | — |
| 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 | 3-{3-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}phenylacetamide | HCID 86627353 | 54% |
Reaction Steps
The title Compound was prepared from Compound 274c following the procedure described for the compound of Example 274 using 3-bromoacetanilide 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 7:3 to 4:6 affording the title product. Orange oil. Yield: 54%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08518916B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-a6bae25e56dc48dda12a8f816d8348c1 |
| Source note | uspto-grants-2013_08 |