HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → 4-((5-Chloropyridin-2-yl)methoxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | (5-Chloropyridin-2-yl)methanol | HCID 20537893 | — |
| Reactant | 1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one | HCID 89690281 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-((5-Chloropyridin-2-yl)methoxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one | HCID 89690396 | 53.1% |
Reaction Steps
To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (100 mg), (5-chloropyridin-2-yl)methanol (102 mg) and tributylphosphine (266 μl) in THF (15 ml) was added 1,1′-(azodicarbonyl)dipiperidine (269 mg) at 60° C., and the mixture was stirred at the same temperature for 3 h. The mixture was diluted with EtOAc, and washed with water and brine. The organic layer was concentrated, and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (76.8 mg) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365540B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-546a92ef3e004cc38638bbe9e983e089 |
| Source note | uspto-grants-2016_06 |