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 57617105 | HCID 57617105 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1-Methylpyrrolidine | HCID 8454 | — |
| Product | HCID 58005143 | HCID 58005143 | 92.1% |
Reaction Steps
To a solution of the product from Step 4 (19.4 g, 41.7 mmol) and 6-bromo-7-methoxy-2-phenylquinolin-4(1H)-one (Step 3, 13.5 g, 40.9 mmol) in N-methylpyrrolidine (200 mL) was added cesium carbonate (20.0 g, 61.3 mmol). The reaction mixture was then heated at 45° C. with stirring for 15 hours and cooled to RT. The reaction mixture was poured into EtOAc and water, and the white solids removed by filtration. The layers were separated, and the organic phase washed with saturated aqueous NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica (gradient elution 10% to 50% EtOAc in hexanes) to give the title compound (21.0 g) as a pale yellow solid. LRMS (M+H)+ Calcd.: 557.1; found 557.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08377874B2 |
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| Source dataset | uspto-grants-2013_02 |
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| ORD ID | ord-0f175e9a63e44596add6b0d783865b9b |
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| Source note | uspto-grants-2013_02 |
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