Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | Methyl 2-(7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate | HCID 54681697 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59340121 | HCID 59340121 | 18.4% |
Reaction Steps
A solution of methyl 2-(7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (100 mg, 271 μmol), Pd2 dba3.CHCl3 (28 mg, 27 μmol), X-Phos (26 mg, 54 μmol) and morpholine (71 μl, 813 μmol) in 1,4-dioxane (3 ml) was treated with sodium tert-butoxide (104 mg, 1084 μmol). The reaction was stirred at 80° C. in a sealed tube. After 24 hours, the suspension was cooled to 23° C., filtered through celite (extensively washing with methanol), the filtrate concentrated in vacuo and purified by silica gel chromatography after adsorption onto silica (eluant: 10% methanol/dichloromethane+1% AcOH), affording 18 mg (18%) of 2-(4-Hydroxy-1-methyl-7-morpholino-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acid as a greenish-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07728130B2 |
|---|
| Source dataset | uspto-grants-2010_06 |
|---|
| ORD ID | ord-ca1e41042f8b4f35a81a3b998b771994 |
|---|
| Source note | uspto-grants-2010_06 |
|---|
