Iodoethane → HCID 70913334, compound

HRID 2208787Notes

Reaction equation

HRID 2208787 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:25](I)[CH3:26]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:25][CH3:26])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 70873719HCID 70873719, compound

Product 1

HCID 70913334HCID 70913334, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-chloro-3-(cyclopentylamino)-2-methylbenzoate (0.62 g, 2.32 mmol) in dry DMF (10 mL), cesium carbonate (3.78 g, 11.6 mmol) and ethyl iodide (5.43 g, 34.8 mmol) were added and the resulting reaction mass was heated at 80° C. for 18 h. On completion, reaction mixture was cooled to room temperature and filtered. The residue was washed with ethyl acetate and filtrate concentrated and purified by column chromatography to afford desired methyl 5-chloro-3-(cyclopentyl(ethyl)amino)-2-methylbenzoate (0.101 g, 15%).

Workup

  1. customthe resulting reaction mass
  2. customOn completion, reaction mixture
  3. temperaturewas cooled to room temperature
  4. filtrationfiltered
  5. washThe residue was washed with ethyl acetate and filtrate
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-31713f62d3244d3ba01019e759d5483f
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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