Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylate | HCID 56590484 | — |
| Reactant | HCID 59287022 | HCID 59287022 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 59287096 | HCID 59287096 | — |
Reaction Steps
To a solution of 3-bromo-7-methoxyquinolin-2(1H)-one (1.31 g, 5.17 mmol) and 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (2.0 g, 4.31 mmol) in NMP (21.5 mL), Cs2CO3 (2.11 g, 6.46 mmol) was added, and the reaction mixture was stirred for 40 hours at 40° C. An additional portion of 1-t-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (1.0 g, 2.16 mmol) was added, and the reaction mixture was stirred at 40° C. for 16 hours. The reaction mixture was cooled and poured onto a mixture of EtOAc and H2O, and the layers were separated. The organic layer was washed with H2O (2×), NaHCO3 (2×) and brine, dried over Mg2SO4, filtered and concentrated. The product was used with no further purification. LRMS (M+H-Boc)+=381.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08377874B2 |
|---|
| Source dataset | uspto-grants-2013_02 |
|---|
| ORD ID | ord-8908648a477f4f618a4a1fe9e6869c0d |
|---|
| Source note | uspto-grants-2013_02 |
|---|