HuagongsheHuagongshe Chemistry Print Report · For research reference only
Morpholine → Methyl 2-methyl-2-(5-morpholino-3-nitropyridin-2-yl)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | 2-Pyridineacetic acid, 5-bromo-alpha,alpha-dimethyl-3-nitro-, methyl ester | HCID 67285217 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Methyl 2-methyl-2-(5-morpholino-3-nitropyridin-2-yl)propanoate | HCID 67285292 | — |
Reaction Steps
A stirred mixture of methyl 2-(5-bromo-3-nitropyridin-2-yl)-2-methylpropanoate (1.2 g, 3.96 mmol), morpholine (0.34 mL, 3.96 mmol), Pd2dba3 (181 mg, 0.20 mmol), XPhos (189 mg, 0.40 mmol) and sodium tert-butoxide (1.1 g, 11.88 mmol) in toluene (30 mL) was heated at reflux for two h. After this time the reaction was cooled to rt and partitioned between EtOAc (300 mL) and water (100 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Column chromatography gave methyl 2-methyl-2-(5-morpholino-3-nitropyridin-2-yl)propanoate as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08765940B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-ae509e17941d44298cc8f7580b9cc086 |
| Source note | uspto-grants-2014_07 |