Iodoethane → Methyl 5-bromo-3-(cyclopentyl(ethyl)amino)-2-methylbenzoate

HRID 1530238Notes

Reaction equation

HRID 1530238 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O-:9])=[O:8].[C:18](=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](I)[CH3:25]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:12]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:24][CH3:25])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:18])=[O:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 866726525-Bromo-3-(cyclopentylamino)-2-methylbenzoate

Product 1

HCID 70872402Methyl 5-bromo-3-(cyclopentyl(ethyl)amino)-2-methylbenzoateYield 32.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 5-bromo-3-(cyclopentylamino)-2-methylbenzoate (2 g, 6.43 mmol) in DMF (15 mL), cesium carbonate (4.18 g, 12.8 mmol) and ethyl iodide (5.01 g, 32.15 mmol) were added; the resulting reaction mixture was heated at 80° C. for 18 h. On completion, the reaction mixture was cooled to room temperature and filtered, residue was washed with ethyl acetate and filtrate was concentrated to afford desired crude compound, which was purified by column chromatography at afford methyl 5-bromo-3-(cyclopentyl(ethyl)amino)-2-methylbenzoate (0.7 g, 32.1%).

Workup

  1. customthe resulting reaction mixture
  2. temperatureOn completion, the reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. washresidue was washed with ethyl acetate and filtrate
  5. concentrationwas concentrated
  6. customto afford desired crude compound, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-24b2072b38b04870b4d5d49fd7b4ba1b
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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