Iodoethane → (S)-ethyl 2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetate

HRID 931732Notes

Reaction equation

HRID 931732 reaction equation
[Br:1][C:2]1[C:11]([C@H:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:13]([OH:15])=[O:14])=[C:10]([CH3:21])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:22])=[N:7]2.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:30][CH3:31]>CN(C=O)C>[Br:1][C:2]1[C:11]([C@H:12]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[C:13]([O:15][CH2:30][CH3:31])=[O:14])=[C:10]([CH3:21])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:22])=[N:7]2

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 66631643(S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetic acid

Product 1

HCID 68586165(S)-ethyl 2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetateYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetic acid (5G) (180 mg, 0.49 mmol) in DMF (15 mL) was added cesium carbonate (321 mg, 0.98 mmol) at 0° C. After being stirred for 10 min iodoethane (0.059 mL, 0.74 mmol) was added. The mixture was stirred at room temperature for 2 hours and quenched by the slow addition of a NaHCO3 solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. The residue was purified by column chromatography to give the pure product 5H (168 mg, 87%). LCMS-ESI+ (m/z): 394.1, 396.1 (M+H)+.

Workup

  1. additionwas added
  2. customquenched by the slow addition of a NaHCO3 solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8c12085d782c4a1eaeda95fd3ceb9f40
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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