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 | HCID 59340074 | HCID 59340074 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59340093 | HCID 59340093 | 11% |
Reaction Steps
A solution of ethyl 2-(6-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (202 mg, 527 μmol), Pd2 dba3.CHCl3 (55 mg, 53 μmol), X-Phos (50 mg, 105 μmol) and morpholine (115 μl, 1318 μmol) in 1,4-dioxane (3 ml) was treated with sodium tert-butoxide (203 mg, 2109 μmol). The reaction was stirred at 80° C. in a sealed tube. After 21 hours, the solution was adsorbed onto silica gel, concentrated in vacuo and purified by silica gel chromatography (eluant: 4% methanol/dichloromethane, followed by/dichloromethane+1% AcOH) and subsequently by RP HPLC (0-100% MeCN/water+1% TFA, 10 min) affording 21 mg (11%) of 2-(4-hydroxy-1-methyl-6-morpholino-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acid as an yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07728130B2 |
|---|
| Source dataset | uspto-grants-2010_06 |
|---|
| ORD ID | ord-1fcd0618a3274b06b0c8c4c104459511 |
|---|
| Source note | uspto-grants-2010_06 |
|---|
