Ethyl Acetate → HCID 58005143, compound

HRID 389189Notes

Reaction equation

HRID 389189 reaction equation
BrC1C=CC(S([O:11][C@@H:12]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)(=O)=O)=CC=1.[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[NH:35][C:34]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[CH:33][C:32]2=O.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CN1CCCC1.O>[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[C:34]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH:33]=[C:32]2[O:11][C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 57617105HCID 57617105, compound

Product 1

HCID 58005143HCID 58005143, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
45 °C

Procedure

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.

Workup

  1. temperaturecooled to RT
  2. customthe white solids removed by filtration
  3. customThe layers were separated
  4. washthe organic phase washed with saturated aqueous NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica (gradient elution 10% to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0f175e9a63e44596add6b0d783865b9b
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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