HuagongsheHuagongshe Chemistry Print Report · For research reference only
Morpholine → 4-(6-Bromopyridin-3-yl)morpholine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 2-Bromo-5-iodopyridine | HCID 4738271 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(6-Bromopyridin-3-yl)morpholine | HCID 23092131 | — |
Reaction Steps
Tris(dibenzylideneacetone)dipalladium (840 mg) and 4,5-bis(diphenyl-phosphino)-9,9-dimethylxanthene (1.6 g) and sodium tert-butoxide (6.6 g) were added to a solution of morpholine (2 ml) and 2-bromo-5-iodo-pyridine (7.8 g) in toluene (230 ml), and the mixture was stirred under nitrogen atmosphere at room temperature overnight. Water and ethyl acetate were added to the mixture and the organic layer was separated, washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=9:1→7:3) to give the titled compound (5.07 g). MS (m/z): 243/245 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08084611B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-53b301b4ef07439286be831dcb394ad9 |
| Source note | uspto-grants-2011_12 |