HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-(6-Methylpyridin-2-yl)-1-[1-(3-nitropyridin-2-yl)piperidin-4-yl]prop-2-yn-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromo-3-nitropyridine | HCID 555054 | — |
| Reactant | 3-(6-Methyl-pyridin-2-yl)-1-piperidin-4-yl-prop-2-yn-1-ol | HCID 68977495 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | 3-(6-Methylpyridin-2-yl)-1-[1-(3-nitropyridin-2-yl)piperidin-4-yl]prop-2-yn-1-ol | HCID 68724618 | 74.2% |
Reaction Steps
A well homogenised mixture of Compound 237a (200 mg, 0.86 mmol), 2-bromo-3-nitropyridine (194 mg, 0.95 mmol) and triethylamine (249 μL, 1.74 mmol) in N,N-dimethylacetamide (15 mL) was stirred at r.t. for 4 h. Afterwards, the reaction mixture was poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography eluting with Petroleum Ether-EtOAc 7:3, affording the title product (225 mg) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08518916B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-2142db12e38e4ba88e795be5a27ccf19 |
| Source note | uspto-grants-2013_08 |