Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(4-Bromophenyl)morpholine | HCID 11622851 | — |
| Reactant | HCID 178446061 | HCID 178446061 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 10435982 | HCID 10435982 | — |
Reaction Steps
To a solution of N-(4-bromophenyl)morpholine (0.66 mmol, 159 mg) in DMF (7 mL) was added under a stream of nitrogen (2S)-N-(cyanomethyl)-4-methyl-2-{phenyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methoxy}pentanamide from Example 16 (0.66 mmol, 250 mg). PdCl2(dppf) (0.033 mmol, 24 mg) and 2N Na2CO3 (2.63 mmol) was added. The mixture was degassed with a rapid stream of nitrogen bubbling through the mixture and the mixture was heated to 85° C. for 18 h. EtOAc was added, the mixture was washed with water and brine. The organic extract was dried and chromatographed (20-40% EtOAc/hexane) to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07279478B2 |
|---|
| Source dataset | uspto-grants-2007_10 |
|---|
| ORD ID | ord-c77f2e71866f424997f27147b945b5e3 |
|---|
| Source note | uspto-grants-2007_10 |
|---|
