HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chloro-6-methyl-3-nitropyridine → 6-Methyl-2-[4-[3-(6-bromo-2-pyridyl)prop-2-ynylidene]piperidin-1-yl]nicotinonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Chloro-6-methyl-3-nitropyridine | HCID 1268230 | — |
| Reactant | 3-(6-Methyl-pyridin-2-yl)-1-piperidin-4-yl-prop-2-yn-1-ol | HCID 68977495 | — |
| Reactant | 2-Bromo-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine | HCID 87642212 | — |
| Product | 6-Methyl-2-[4-[3-(6-bromo-2-pyridyl)prop-2-ynylidene]piperidin-1-yl]nicotinonitrile | HCID 87641638 | 95% |
Reaction Steps
The title compound was prepared as described for the compound of Example 237 but starting from Compound 305b instead of compound 237a and 2-chloro-6-methyl-3-nitropyridine instead of 2-bromo-3-nitropyridine. An additional equivalent of TEA was used. After the work-up, the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc gradient from PE:EtAc 95:5 to 6:4 affording the title product. Yellow oil. Yield: 95%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08518916B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-6644481c14944a898d4c77ea8239f089 |
| Source note | uspto-grants-2013_08 |